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868540-16-3

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  • High quality (alphaS)-alpha-[(4-Morpholinylacetyl)aMino]benzenebutanoyl-L-leucyl-L-phenylalanine supplier in China

    Cas No: 868540-16-3

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  • High purity (alphaS)-alpha-[(4-Morpholinylacetyl)amino]benzenebutanoyl-L-leucyl-L-phenylalanine CAS No.:868540-16-3

    Cas No: 868540-16-3

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  • (S)-2-{(S)-4-methyl-2-[(S)-2-(2-morpholinoacetamido)-4-phenylbutanamido]-pentanamido}-3-phenylpropanoic acid

    Cas No: 868540-16-3

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868540-16-3 Usage

Uses

(S)-2-((S)-4-Methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenylpropanoic Acid is an intermediate for Carfilzomib (C183460), which is a second-generation proteasome inhibitor that is used as a treatment in relapsed and refractory multiple myeloma.

Check Digit Verification of cas no

The CAS Registry Mumber 868540-16-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,6,8,5,4 and 0 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 868540-16:
(8*8)+(7*6)+(6*8)+(5*5)+(4*4)+(3*0)+(2*1)+(1*6)=203
203 % 10 = 3
So 868540-16-3 is a valid CAS Registry Number.

868540-16-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

1.2 Other means of identification

Product number -
Other names (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenylpropanoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:868540-16-3 SDS

868540-16-3Synthetic route

(S)-benzyl 2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido) pentanamido)-3-phenylpropanoate
875309-92-5

(S)-benzyl 2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido) pentanamido)-3-phenylpropanoate

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
With methanol; hydrogen; palladium 10% on activated carbon In ethyl acetate under 760.051 Torr; for 2h;
With palladium on activated charcoal; ammonium formate In methanol at 25 - 30℃; for 2h; Solvent; Reagent/catalyst;77 g
With 5 mol% Pd/C; hydrogen In methanol for 0.5h;
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0 °C / Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C
2.2: 0 - 20 °C / Inert atmosphere
3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
3.2: 0 - 20 °C / Inert atmosphere
4.1: potassium iodide / tetrahydrofuran / Inert atmosphere
5.1: lithium hydroxide / methanol; water / 12 h / 0 - 5 °C
View Scheme
Multi-step reaction with 6 steps
1: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
2: hydrogenchloride / isopropyl alcohol / 2 h / 25 - 30 °C
3: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
4: hydrogenchloride / ethyl acetate / 2 h / 25 - 30 °C
5: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
6: lithium hydroxide monohydrate; water / tetrahydrofuran / 3 h / 25 - 30 °C
View Scheme
Multi-step reaction with 4 steps
1.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 - 30 °C
2.1: trifluoroacetic acid / dichloromethane / 2 h / 2 - 30 °C
2.2: 2 - 30 °C
3.1: trifluoroacetic acid / dichloromethane / 2 h / 2 - 30 °C
3.2: 2 - 30 °C
4.1: ammonium formate; palladium on activated charcoal / methanol / 2 h / 25 - 30 °C
View Scheme
Multi-step reaction with 5 steps
1.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 - 30 °C
2.1: dichloromethane / 2 h / 0 - 30 °C
3.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 0 - 30 °C / Inert atmosphere
4.1: trifluoroacetic acid / dichloromethane / 2 h / 2 - 30 °C
4.2: 2 - 30 °C
5.1: ammonium formate; palladium on activated charcoal / methanol / 2 h / 25 - 30 °C
View Scheme
Multi-step reaction with 6 steps
1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / dichloromethane / 18 h / 20 °C
2: dichloromethane / 1 h / 20 °C
3: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / dichloromethane / 18 h / 20 °C
4: dichloromethane / 1 h / 20 °C
5: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / dichloromethane / 18 h / 20 °C
6: 5 mol% Pd/C; hydrogen / methanol / 0.5 h
View Scheme
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0 °C / Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C
2.2: 0 - 20 °C / Inert atmosphere
3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
3.2: 0 - 20 °C / Inert atmosphere
4.1: potassium iodide / tetrahydrofuran / Inert atmosphere
5.1: lithium hydroxide / methanol; water / 12 h / 0 - 5 °C
View Scheme
Multi-step reaction with 6 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
2: dichloromethane / 3 h / 0 - 20 °C
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
4: dichloromethane / 3 h / 0 - 20 °C
5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
6: lithium hydroxide monohydrate / methanol / 3 h / 0 - 20 °C
View Scheme
(N-(tert-butoxycarbonyl)-L-leucinyl)-L-phenylalanine methyl ester
15136-32-0, 87976-66-7, 120342-25-8, 5874-73-7

(N-(tert-butoxycarbonyl)-L-leucinyl)-L-phenylalanine methyl ester

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C
1.2: 0 - 20 °C / Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
2.2: 0 - 20 °C / Inert atmosphere
3.1: potassium iodide / tetrahydrofuran / Inert atmosphere
4.1: lithium hydroxide / methanol; water / 12 h / 0 - 5 °C
View Scheme
Multi-step reaction with 5 steps
1: hydrogenchloride / isopropyl alcohol / 2 h / 25 - 30 °C
2: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
3: hydrogenchloride / ethyl acetate / 2 h / 25 - 30 °C
4: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
5: lithium hydroxide monohydrate; water / tetrahydrofuran / 3 h / 25 - 30 °C
View Scheme
Multi-step reaction with 5 steps
1: dichloromethane / 3 h / 0 - 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
3: dichloromethane / 3 h / 0 - 20 °C
4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
5: lithium hydroxide monohydrate / methanol / 3 h / 0 - 20 °C
View Scheme
(S)-methyl 2-((S)-2-tert.butoxycarbonyIamino-4-phenylbutanamido-4-methylpentanamido)-3-phenylpropanoate
868539-96-2

(S)-methyl 2-((S)-2-tert.butoxycarbonyIamino-4-phenylbutanamido-4-methylpentanamido)-3-phenylpropanoate

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
1.2: 0 - 20 °C / Inert atmosphere
2.1: potassium iodide / tetrahydrofuran / Inert atmosphere
3.1: lithium hydroxide / methanol; water / 12 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / ethyl acetate / 2 h / 25 - 30 °C
2: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
3: lithium hydroxide monohydrate; water / tetrahydrofuran / 3 h / 25 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1: dichloromethane / 3 h / 0 - 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
3: lithium hydroxide monohydrate / methanol / 3 h / 0 - 20 °C
View Scheme
C28H36ClN3O5
868540-08-3

C28H36ClN3O5

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium iodide / tetrahydrofuran / Inert atmosphere
2: lithium hydroxide / methanol; water / 12 h / 0 - 5 °C
View Scheme
C32H44N4O6

C32H44N4O6

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
With lithium hydroxide In methanol; water at 0 - 5℃; for 12h;
With lithium hydroxide monohydrate; water In tetrahydrofuran at 25 - 30℃; for 3h;48.0 g
With lithium hydroxide monohydrate In methanol at 0 - 20℃; for 3h;
(S)-methyl 2-((S)-2-amino-4-methylpentanamido)-3-phenylpropanoate hydrochloride
6461-07-0

(S)-methyl 2-((S)-2-amino-4-methylpentanamido)-3-phenylpropanoate hydrochloride

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
2: hydrogenchloride / ethyl acetate / 2 h / 25 - 30 °C
3: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
4: lithium hydroxide monohydrate; water / tetrahydrofuran / 3 h / 25 - 30 °C
View Scheme
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
2: hydrogenchloride / ethyl acetate / 2 h / 25 - 30 °C
3: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
4: lithium hydroxide monohydrate; water / tetrahydrofuran / 3 h / 25 - 30 °C
View Scheme
(S)-methyl 2-((S)-2-((S)-2-amino-4-phenyIbutanamido)-4-methylpentanamido)-3-phenylpropanoate hydrochloride

(S)-methyl 2-((S)-2-((S)-2-amino-4-phenyIbutanamido)-4-methylpentanamido)-3-phenylpropanoate hydrochloride

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
2: lithium hydroxide monohydrate; water / tetrahydrofuran / 3 h / 25 - 30 °C
View Scheme
L-leucine
61-90-5

L-leucine

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: sodium hydroxide / water / 20 h / 25 - 30 °C
2: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
3: hydrogenchloride / isopropyl alcohol / 2 h / 25 - 30 °C
4: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
5: hydrogenchloride / ethyl acetate / 2 h / 25 - 30 °C
6: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
7: lithium hydroxide monohydrate; water / tetrahydrofuran / 3 h / 25 - 30 °C
View Scheme
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride
7524-50-7

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
2: hydrogenchloride / isopropyl alcohol / 2 h / 25 - 30 °C
3: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
4: hydrogenchloride / ethyl acetate / 2 h / 25 - 30 °C
5: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
6: lithium hydroxide monohydrate; water / tetrahydrofuran / 3 h / 25 - 30 °C
View Scheme
L-phenylalanine
63-91-2

L-phenylalanine

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: thionyl chloride / 8 h / 25 - 30 °C
2: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
3: hydrogenchloride / isopropyl alcohol / 2 h / 25 - 30 °C
4: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
5: hydrogenchloride / ethyl acetate / 2 h / 25 - 30 °C
6: benzotriazol-1-ol; 4-methyl-morpholine; dicyclohexyl-carbodiimide / dichloromethane / 2 h / 0 - 30 °C / Inert atmosphere
7: lithium hydroxide monohydrate; water / tetrahydrofuran / 3 h / 25 - 30 °C
View Scheme
(x)C2HF3O2*C22H28N2O3

(x)C2HF3O2*C22H28N2O3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 0 - 30 °C / Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / 2 h / 2 - 30 °C
2.2: 2 - 30 °C
3.1: ammonium formate; palladium on activated charcoal / methanol / 2 h / 25 - 30 °C
View Scheme
L-phenylalanine benzyl ester hydrochloride
2462-32-0

L-phenylalanine benzyl ester hydrochloride

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 - 30 °C
2.1: trifluoroacetic acid / dichloromethane / 2 h / 2 - 30 °C
2.2: 2 - 30 °C
3.1: trifluoroacetic acid / dichloromethane / 2 h / 2 - 30 °C
3.2: 2 - 30 °C
4.1: ammonium formate; palladium on activated charcoal / methanol / 2 h / 25 - 30 °C
View Scheme
Multi-step reaction with 5 steps
1.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 - 30 °C
2.1: dichloromethane / 2 h / 0 - 30 °C
3.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 0 - 30 °C / Inert atmosphere
4.1: trifluoroacetic acid / dichloromethane / 2 h / 2 - 30 °C
4.2: 2 - 30 °C
5.1: ammonium formate; palladium on activated charcoal / methanol / 2 h / 25 - 30 °C
View Scheme
Multi-step reaction with 6 steps
1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / dichloromethane / 18 h / 20 °C
2: dichloromethane / 1 h / 20 °C
3: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / dichloromethane / 18 h / 20 °C
4: dichloromethane / 1 h / 20 °C
5: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / dichloromethane / 18 h / 20 °C
6: 5 mol% Pd/C; hydrogen / methanol / 0.5 h
View Scheme
(S)-benzyl 2-((S)-2-(tert-butoxycarbonylamino)-4-methylpentanamido)-3-phenylpropanoate
140834-91-9, 70637-26-2

(S)-benzyl 2-((S)-2-(tert-butoxycarbonylamino)-4-methylpentanamido)-3-phenylpropanoate

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: trifluoroacetic acid / dichloromethane / 2 h / 2 - 30 °C
1.2: 2 - 30 °C
2.1: trifluoroacetic acid / dichloromethane / 2 h / 2 - 30 °C
2.2: 2 - 30 °C
3.1: ammonium formate; palladium on activated charcoal / methanol / 2 h / 25 - 30 °C
View Scheme
Multi-step reaction with 4 steps
1.1: dichloromethane / 2 h / 0 - 30 °C
2.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 0 - 30 °C / Inert atmosphere
3.1: trifluoroacetic acid / dichloromethane / 2 h / 2 - 30 °C
3.2: 2 - 30 °C
4.1: ammonium formate; palladium on activated charcoal / methanol / 2 h / 25 - 30 °C
View Scheme
Multi-step reaction with 5 steps
1: dichloromethane / 1 h / 20 °C
2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / dichloromethane / 18 h / 20 °C
3: dichloromethane / 1 h / 20 °C
4: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / dichloromethane / 18 h / 20 °C
5: 5 mol% Pd/C; hydrogen / methanol / 0.5 h
View Scheme
morpholin-4-ylacetic acid
3235-69-6

morpholin-4-ylacetic acid

Fmoc-phenylalanine-2-chlorotrityl resin

Fmoc-phenylalanine-2-chlorotrityl resin

Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

N-(fluorenyl-9-methoxycarbonyl)-L-homophenylalanine
132684-59-4

N-(fluorenyl-9-methoxycarbonyl)-L-homophenylalanine

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Stage #1: Fmoc-phenylalanine-2-chlorotrityl resin With piperidine In N,N-dimethyl-formamide solid-phase peptide synthesis;
Stage #2: Fmoc-Leu-OH With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide solid-phase peptide synthesis;
Stage #3: morpholin-4-ylacetic acid; N-(fluorenyl-9-methoxycarbonyl)-L-homophenylalanine Further stages;
(S)-benzyl 2-((S)-2-amino-4-methylpentanamido)-3-phenylpropanoate TFA salt
70637-28-4

(S)-benzyl 2-((S)-2-amino-4-methylpentanamido)-3-phenylpropanoate TFA salt

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / dichloromethane / 18 h / 20 °C
2: dichloromethane / 1 h / 20 °C
3: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / dichloromethane / 18 h / 20 °C
4: 5 mol% Pd/C; hydrogen / methanol / 0.5 h
View Scheme
(S)-benzyl 2-((S)-2-((S)-2-(tert-butoxycarbonylamino)-4-phenylbutanamido)-4-methylpentanamido)-3-phenylpropanoate
868540-15-2

(S)-benzyl 2-((S)-2-((S)-2-(tert-butoxycarbonylamino)-4-phenylbutanamido)-4-methylpentanamido)-3-phenylpropanoate

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dichloromethane / 1 h / 20 °C
2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / dichloromethane / 18 h / 20 °C
3: 5 mol% Pd/C; hydrogen / methanol / 0.5 h
View Scheme
C2HF3O2*C32H39N3O4
875309-83-4

C2HF3O2*C32H39N3O4

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / dichloromethane / 18 h / 20 °C
2: 5 mol% Pd/C; hydrogen / methanol / 0.5 h
View Scheme
Leu-Phe-OMe trifluoroacetate

Leu-Phe-OMe trifluoroacetate

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
2: dichloromethane / 3 h / 0 - 20 °C
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
4: lithium hydroxide monohydrate / methanol / 3 h / 0 - 20 °C
View Scheme
C2HF3O2*C26H35N3O4
868539-99-5

C2HF3O2*C26H35N3O4

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
2: lithium hydroxide monohydrate / methanol / 3 h / 0 - 20 °C
View Scheme
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: thionyl chloride / 2 h / 0 - 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
3: dichloromethane / 3 h / 0 - 20 °C
4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
5: dichloromethane / 3 h / 0 - 20 °C
6: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
7: lithium hydroxide monohydrate / methanol / 3 h / 0 - 20 °C
View Scheme
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

C9H17NO2*C4HF7O2

C9H17NO2*C4HF7O2

carfilzomib

carfilzomib

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; diethylamine In N,N-dimethyl-formamide at -5℃; for 1.5h;88%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

C9H17NO2*C2HF3O2

C9H17NO2*C2HF3O2

(S)-4-methyl-N-((S)-1-(((S)-1-((R)-2-methyloxiran-2-yl)-1-oxohexan-2-yl) amino)-1-oxo-3-phenylpropan-2-yl)-2-((S)-2-(2-morpholinoacetamido)-4-phenyl butanamido)pentanamide

(S)-4-methyl-N-((S)-1-(((S)-1-((R)-2-methyloxiran-2-yl)-1-oxohexan-2-yl) amino)-1-oxo-3-phenylpropan-2-yl)-2-((S)-2-(2-morpholinoacetamido)-4-phenyl butanamido)pentanamide

Conditions
ConditionsYield
Stage #1: (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid With benzotriazol-1-ol In dichloromethane for 0.333333h;
Stage #2: C9H17NO2*C2HF3O2 With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12.5h; Cooling;
87%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

C9H17NO2*C3HF5O2

C9H17NO2*C3HF5O2

carfilzomib

carfilzomib

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; diethylamine In N,N-dimethyl-formamide at -5℃; for 1.5h; Temperature; Reagent/catalyst;86%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

(2R,4S)-4-((tert-butoxycarbonyl)amino)-2-hydroxy-2,6-dimethyl-3-oxoheptyl 3-(prop-2-yn-1-yloxy)propane-1-sulfonate

(2R,4S)-4-((tert-butoxycarbonyl)amino)-2-hydroxy-2,6-dimethyl-3-oxoheptyl 3-(prop-2-yn-1-yloxy)propane-1-sulfonate

(4S,7S,10S,13S,15R)-10-benzyl-15-hydroxy-7,13-diisobutyl-15-methyl-1-morpholino-2,5,8,11,14-pentaoxo-4-phenethyl-3,6,9,12-tetraazahexadecan-16-yl 3-(prop-2-yn-1-ylcarbamoyl)benzenesulfonate
1541172-80-8

(4S,7S,10S,13S,15R)-10-benzyl-15-hydroxy-7,13-diisobutyl-15-methyl-1-morpholino-2,5,8,11,14-pentaoxo-4-phenethyl-3,6,9,12-tetraazahexadecan-16-yl 3-(prop-2-yn-1-ylcarbamoyl)benzenesulfonate

Conditions
ConditionsYield
Stage #1: (2R,4S)-4-((tert-butoxycarbonyl)amino)-2-hydroxy-2,6-dimethyl-3-oxoheptyl 3-(prop-2-yn-1-yloxy)propane-1-sulfonate With hydrogenchloride In 1,4-dioxane at 20℃; for 1h;
Stage #2: (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.5h;
80%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

(S)-2-amino-1-((R)-2-methyloxiran-2-yl)-3-phenylpropan-1-one trifluoroacetate
1148157-29-2

(S)-2-amino-1-((R)-2-methyloxiran-2-yl)-3-phenylpropan-1-one trifluoroacetate

(S)-4-methyl-N-((S)-1-(((S)-1-((R)-2-methyloxiran-2-yl)-1-oxo-3-phenylpropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)-2-((S)-2-(2-morpholinoacetamido)-4-phenyl butanamido)pentanamide

(S)-4-methyl-N-((S)-1-(((S)-1-((R)-2-methyloxiran-2-yl)-1-oxo-3-phenylpropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)-2-((S)-2-(2-morpholinoacetamido)-4-phenyl butanamido)pentanamide

Conditions
ConditionsYield
Stage #1: (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid With benzotriazol-1-ol In dichloromethane for 0.333333h;
Stage #2: (S)-2-amino-1-((R)-2-methyloxiran-2-yl)-3-phenylpropan-1-one trifluoroacetate With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12.5h; Cooling;
80%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

C13H17NO2*C2HF3O2

C13H17NO2*C2HF3O2

(S)-4-methyl-N-((S)-1-(((S)-1-((R)-2-methyloxiran-2-yl)-1-oxo-4-phenylbutan-2 -yl)amino)-1-oxo-3-phenylpropan-2-yl)-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamide

(S)-4-methyl-N-((S)-1-(((S)-1-((R)-2-methyloxiran-2-yl)-1-oxo-4-phenylbutan-2 -yl)amino)-1-oxo-3-phenylpropan-2-yl)-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamide

Conditions
ConditionsYield
Stage #1: (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid With benzotriazol-1-ol In dichloromethane for 0.333333h;
Stage #2: C13H17NO2*C2HF3O2 With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12.5h; Cooling;
76%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

C7H13NO2*C2HF3O2

C7H13NO2*C2HF3O2

(S)-4-methyl-N-((S)-1-(((S)-1-((R)-2-methyloxiran-2-yl)-1-oxobutan-2-yl) amino)-1-oxo-3-phenylpropan-2-yl)-2-((S)-2-(2-morpholinoacetamido)-4-phenyl butanamido)pentanamide

(S)-4-methyl-N-((S)-1-(((S)-1-((R)-2-methyloxiran-2-yl)-1-oxobutan-2-yl) amino)-1-oxo-3-phenylpropan-2-yl)-2-((S)-2-(2-morpholinoacetamido)-4-phenyl butanamido)pentanamide

Conditions
ConditionsYield
Stage #1: (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid With benzotriazol-1-ol In dichloromethane for 0.333333h;
Stage #2: C7H13NO2*C2HF3O2 With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12.5h; Cooling;
73%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

C16H21NO5S*ClH

C16H21NO5S*ClH

trifluoroacetic acid
76-05-1

trifluoroacetic acid

C47H61N5O10S*C2HF3O2

C47H61N5O10S*C2HF3O2

Conditions
ConditionsYield
Stage #1: (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0℃; for 0.333333h;
Stage #2: C16H21NO5S*ClH In dichloromethane at 0℃; for 0.166667h;
Stage #3: trifluoroacetic acid With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃;
60%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

C12H19NO3S*ClH

C12H19NO3S*ClH

trifluoroacetic acid
76-05-1

trifluoroacetic acid

C43H59N5O8S*C2HF3O2

C43H59N5O8S*C2HF3O2

Conditions
ConditionsYield
Stage #1: (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0℃; for 0.333333h;
Stage #2: C12H19NO3S*ClH In dichloromethane at 0℃; for 0.166667h;
Stage #3: trifluoroacetic acid With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃;
53%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

C2HF3O2*C10H19NO3

C2HF3O2*C10H19NO3

(S)-N-((S)-1-((S)-1-((S)-2-(methoxymethyl)oxiran-2-yl)-4-methyl-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamide

(S)-N-((S)-1-((S)-1-((S)-2-(methoxymethyl)oxiran-2-yl)-4-methyl-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;48%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

L-Leu-[CH2SO2]-DFHMC . HC1

L-Leu-[CH2SO2]-DFHMC . HC1

MorphAc-hPhe-Leu-Phe-W-[CH2SO2]-DFHMC . TFA

MorphAc-hPhe-Leu-Phe-W-[CH2SO2]-DFHMC . TFA

Conditions
ConditionsYield
Stage #1: (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0℃; for 0.333333h;
Stage #2: L-Leu-[CH2SO2]-DFHMC . HC1 In dichloromethane at 0℃; for 0.166667h;
Stage #3: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;
47.3%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

L-Leu-[CH2SO2]-DFHMC . HC1

L-Leu-[CH2SO2]-DFHMC . HC1

trifluoroacetic acid
76-05-1

trifluoroacetic acid

C47H59F2N5O10S*C2HF3O2

C47H59F2N5O10S*C2HF3O2

Conditions
ConditionsYield
Stage #1: (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0℃; for 0.333333h;
Stage #2: L-Leu-[CH2SO2]-DFHMC . HC1 In dichloromethane at 0℃; for 0.166667h;
Stage #3: trifluoroacetic acid With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃;
47%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

C25H35NO3Si*C2HF3O2

C25H35NO3Si*C2HF3O2

(S)-N-((S)-1-((S)-1-((S)-2-((tert-butyldiphenylsilyloxy)methyl)oxiran-2-yl)-4-methyl-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamide

(S)-N-((S)-1-((S)-1-((S)-2-((tert-butyldiphenylsilyloxy)methyl)oxiran-2-yl)-4-methyl-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;45%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

C12H14F5NO3S*ClH

C12H14F5NO3S*ClH

trifluoroacetic acid
76-05-1

trifluoroacetic acid

C43H54F5N5O8S*C2HF3O2

C43H54F5N5O8S*C2HF3O2

Conditions
ConditionsYield
Stage #1: (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0℃; for 0.333333h;
Stage #2: C12H14F5NO3S*ClH In dichloromethane at 0℃; for 0.166667h;
Stage #3: trifluoroacetic acid With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃;
36%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

C16H20FNO5S*ClH

C16H20FNO5S*ClH

trifluoroacetic acid
76-05-1

trifluoroacetic acid

C47H60FN5O10S*C2HF3O2

C47H60FN5O10S*C2HF3O2

Conditions
ConditionsYield
Stage #1: (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0℃; for 0.333333h;
Stage #2: C16H20FNO5S*ClH In dichloromethane at 0℃; for 0.166667h;
Stage #3: trifluoroacetic acid With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃;
31%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

C12H16F3NO3S*ClH

C12H16F3NO3S*ClH

trifluoroacetic acid
76-05-1

trifluoroacetic acid

C43H56F3N5O8S*C2HF3O2

C43H56F3N5O8S*C2HF3O2

Conditions
ConditionsYield
Stage #1: (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0℃; for 0.333333h;
Stage #2: C12H16F3NO3S*ClH In dichloromethane at 0℃; for 0.166667h;
Stage #3: trifluoroacetic acid With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃;
23%
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

carfilzomib

carfilzomib

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 5℃;
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

(S)-2-amino-4-methyl-1-((R)-2-methyloxiran-2-yl)pentan-1-one trifluoroacetic acid salt

(S)-2-amino-4-methyl-1-((R)-2-methyloxiran-2-yl)pentan-1-one trifluoroacetic acid salt

(x)C6H8O7*C40H57N5O7

(x)C6H8O7*C40H57N5O7

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 1.5 h / 0 - 5 °C
2: tetrahydrofuran; acetonitrile / 2 h / 20 °C
View Scheme
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

(S)-2-amino-4-methyl-1-((R)-2-methyloxiran-2-yl)pentan-1-one trifluoroacetic acid salt

(S)-2-amino-4-methyl-1-((R)-2-methyloxiran-2-yl)pentan-1-one trifluoroacetic acid salt

carfilzomib

carfilzomib

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 5℃; for 1.5h; Reagent/catalyst; Temperature; Solvent; stereoselective reaction;230 g
With 4-methyl-morpholine; benzotriazol-1-ol; HATU In N,N-dimethyl-formamide at 0 - 5℃; for 3h; Inert atmosphere;100.0 g
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 5℃; Inert atmosphere;0.08 g
Multi-step reaction with 2 steps
1.1: benzotriazol-1-ol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / -10 - -5 °C
1.2: 0.5 h / 25 - 30 °C
2.1: sodium hydrogencarbonate / dichloromethane; water / 0.17 h / 2 - 6 °C
View Scheme
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

C9H17NO2*CH2O2

C9H17NO2*CH2O2

(x)C6H8O7*C40H57N5O7

(x)C6H8O7*C40H57N5O7

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / 1 h / 0 °C
2: tetrahydrofuran; acetonitrile / 2 h / 20 °C
View Scheme
(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid
868540-16-3

(S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid

C9H17NO2*CH2O2

C9H17NO2*CH2O2

carfilzomib

carfilzomib

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine at 0℃; for 1h;

868540-16-3Downstream Products

868540-16-3Relevant articles and documents

Preparation and biological evaluation of soluble tetrapeptide epoxyketone proteasome inhibitors

Lei, Meng,Zhang, Haoyang,Miao, Hang,Du, Xiao,Zhou, Hui,Wang, Jia,Wang, Xueyuan,Feng, Huayun,Shi, Jingmiao,Liu, Zhaogang,Shen, Jian,Zhu, Yongqiang

, p. 4151 - 4162 (2019/08/07)

A series of novel tetrapeptidyl epoxyketone inhibitors of 20S proteasome was designed and synthesized. To fully understand the SAR, various groups at R1, R2, R3, R4 and R5 positions, including aromatic and aliphatic substituents were designed, synthesized and biologically assayed. Based on the enzymatic results, seven compounds were selected to evaluate their cellular activities and soluble compound 36 showed strong potency against human multiple myeloma (MM) cell lines. Microsomal stability results indicated that compound 36 was more stable in mice, rat and human microsomes than marketed carfilzomib. The in vivo activities of this compound were evaluated with the xenograft mice models of MM cell lines ARH77 and RPMI-8226 with luciferase expression and the T/C value of the two models were 49.5% and 37.6%, respectively. To evaluate the potential cardiovascular toxicity, inhibition of hERG ion channel in HEK293 cells by compound 36 and carfilzomib was carried out. The results indicated that 36 had no binding affinity for the hERG ion channel while carfilzomib could bind it with IC50 of 92.1 μM.

AN IMPROVED PROCESSES FOR THE PREPARATION OF CARFILZOMIB OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

-

, (2016/12/07)

The present invention relates to an improved process for the preparation of carfilzomib or a pharmaceutically acceptable salt thereof. The present invention also relates to a process for the preparation of amorphous form of carfilzomib.

Tunable Probes with Direct Fluorescence Signals for the Constitutive and Immunoproteasome

Dubiella, Christian,Cui, Haissi,Groll, Michael

supporting information, p. 13330 - 13334 (2016/10/30)

Electrophiles are commonly used for the inhibition of proteases. Notably, inhibitors of the proteasome, a central determinant of cellular survival and a target of several FDA-approved drugs, are mainly characterized by the reactivity of their electrophilic head groups. We aimed to tune the inhibitory strength of peptidic sulfonate esters by varying the leaving groups. Indeed, proteasome inhibition correlated well with the pKaof the leaving group. The use of fluorophores as leaving groups enabled us to design probes that release a stoichiometric fluorescence signal upon reaction, thereby directly linking proteasome inactivation to the readout. This principle could be applicable to other sulfonyl fluoride based inhibitors and allows the design of sensitive probes for enzymatic studies.

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