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Val-cit-PAB-OH
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Val-cit-PAB-OH,159857-79-1
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(S)-2-((S)-2-amino-3-methylbutanamido)-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide with best price CAS NO.159857-79-1
Cas No: 159857-79-1
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(S)-2-((S)-2-amino-3-methylbutanamido)-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide
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Val-Cit-PAB
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159857-79-1 Usage

159857-79-1Synthetic route

(9H-fluorenyl)methyl ((S)-1-(((S)-1-(((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidovalerylamido-2-yl)amino))-3-methylbutyramido-2-yl)-carbamate
159858-22-7

(9H-fluorenyl)methyl ((S)-1-(((S)-1-(((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidovalerylamido-2-yl)amino))-3-methylbutyramido-2-yl)-carbamate

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
With diethylamine In N,N-dimethyl-formamide for 24h;100%
With diethylamine In N,N-dimethyl-formamide for 2h;96%
With diethylamine In N,N-dimethyl-formamide for 2h;96%
(9H-fluoren-9-yl)methyl (S)-(1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamate
870487-04-0

(9H-fluoren-9-yl)methyl (S)-(1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamate

Fmoc-Val-OPfp
86060-87-9

Fmoc-Val-OPfp

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Stage #1: (S)-(9H-fluoren-9-yl)methyl (1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamate With piperidine In N,N-dimethyl-formamide at 23℃; for 3h;
Stage #2: Fmoc-Val-OPfp With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 24h;
Stage #3: With piperidine In N,N-dimethyl-formamide at 23℃; for 1h;
93%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide
2: sodium hydrogencarbonate / water; tetrahydrofuran
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide
4: diethylamine / 1-methyl-pyrrolidin-2-one
View Scheme
Multi-step reaction with 3 steps
1.1: dicyclohexyl-carbodiimide; 1-hydroxy-pyrrolidine-2,5-dione / tetrahydrofuran / 16 h / 20 °C
1.2: 16 h / 20 °C
2.1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 36 h / 20 °C
3.1: piperidine / N,N-dimethyl-formamide / 2 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: dicyclohexyl-carbodiimide / acetonitrile; tetrahydrofuran / 24 h / 0 - 20 °C
2: sodium hydrogencarbonate / tetrahydrofuran; 1,2-dimethoxyethane; water / 24 h / 20 °C
3: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 48 h / 20 °C / Darkness
4: diethylamine / 24 h / 20 °C
View Scheme
2,5-dioxopyrrolidin-1-yl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate
130878-68-1

2,5-dioxopyrrolidin-1-yl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / water; tetrahydrofuran
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide
3: diethylamine / 1-methyl-pyrrolidin-2-one
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 3 h / 20 °C
2: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
2: diethylamine / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C / Inert atmosphere
View Scheme
(S)-2-((S)-2-((((9H-fluoren-9-yl)-methoxy)carbonyl)amino)-3-methylbutanamido)-5-ureidopentanoic acid
159858-21-6

(S)-2-((S)-2-((((9H-fluoren-9-yl)-methoxy)carbonyl)amino)-3-methylbutanamido)-5-ureidopentanoic acid

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide
2: diethylamine / 1-methyl-pyrrolidin-2-one
View Scheme
Multi-step reaction with 2 steps
1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 36 h / 20 °C / Darkness; Inert atmosphere
2: diethylamine / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 36 h / 20 °C
2: piperidine / N,N-dimethyl-formamide / 2 h / 20 °C
View Scheme
4-aminobenzenemethanol
623-04-1

4-aminobenzenemethanol

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide
2: diethylamine / 1-methyl-pyrrolidin-2-one
View Scheme
Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 16 h / 20 °C
2.1: diethylamine / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
3.2: 16 h / 20 °C
4.1: dichloromethane / 3 h / 20 °C
5.1: sodium hydroxide; water / 1,4-dioxane / 3 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 16 h / 20 °C
2.1: diethylamine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: HATU / N,N-dimethyl-formamide / 1 h / 20 °C
3.2: 16 h / 20 °C
4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
4.2: 3 h / 20 °C
View Scheme
(S)-2-amino-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide
1037794-22-1

(S)-2-amino-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 3 h / 20 °C
2: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
1.2: 16 h / 20 °C
2.1: dichloromethane / 3 h / 20 °C
3.1: sodium hydroxide; water / 1,4-dioxane / 3 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: HATU / N,N-dimethyl-formamide / 1 h / 20 °C
1.2: 16 h / 20 °C
2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
2.2: 3 h / 20 °C
View Scheme
(S)-tert-butyl 1-(4-(hydroxymethyl)phenylamino)-1-oxo-5-ureidopentan-2-ylcarbamate
1037793-80-8

(S)-tert-butyl 1-(4-(hydroxymethyl)phenylamino)-1-oxo-5-ureidopentan-2-ylcarbamate

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
2: N,N-dimethyl-formamide / 3 h / 20 °C
3: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
Citrulline
372-75-8

Citrulline

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium carbonate / water; 1,4-dioxane / 2 h / 0 - 20 °C
2: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / methanol; dichloromethane / 16 h / 20 °C / Inert atmosphere
3: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
4: N,N-dimethyl-formamide / 3 h / 20 °C
5: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / 1,2-dimethoxyethane; tetrahydrofuran / 16 h / 20 °C / Inert atmosphere
2: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 36 h / 20 °C / Darkness; Inert atmosphere
3: diethylamine / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: sodium hydrogencarbonate / 1,2-dimethoxyethane; water / 24 h / 20 °C / Inert atmosphere
2: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 30 h / 20 °C / Darkness; Inert atmosphere
3: piperidine / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere
4: N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
5: diethylamine / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C / Inert atmosphere
View Scheme
(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid

(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / methanol; dichloromethane / 16 h / 20 °C / Inert atmosphere
2: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
3: N,N-dimethyl-formamide / 3 h / 20 °C
4: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 16 h / 20 °C
2.1: diethylamine / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
3.2: 16 h / 20 °C
4.1: dichloromethane / 3 h / 20 °C
5.1: sodium hydroxide; water / 1,4-dioxane / 3 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 16 h / 20 °C
2.1: diethylamine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: HATU / N,N-dimethyl-formamide / 1 h / 20 °C
3.2: 16 h / 20 °C
4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
4.2: 3 h / 20 °C
View Scheme
(9H-fluoren-9-yl)methyl (S)-(1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamate
870487-04-0

(9H-fluoren-9-yl)methyl (S)-(1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamate

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
2: N,N-dimethyl-formamide / 3 h / 20 °C
3: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: diethylamine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C
2.1: HATU / N,N-dimethyl-formamide / 1 h / 20 °C
2.2: 16 h / 20 °C
3.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
3.2: 3 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: piperidine / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere
2: N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
3: diethylamine / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C / Inert atmosphere
View Scheme
4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate

4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
With water; sodium hydroxide In 1,4-dioxane at 20℃; for 3h;
(S)-(9H-fluoren-9-yl)methyl(1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamate

(S)-(9H-fluoren-9-yl)methyl(1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamate

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: diethylamine / N,N-dimethyl-formamide / 1 h / 20 °C
2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
2.2: 16 h / 20 °C
3.1: dichloromethane / 3 h / 20 °C
4.1: sodium hydroxide; water / 1,4-dioxane / 3 h / 20 °C
View Scheme
tert-butyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentane-2-yl)amino)-3-methyl-1-oxobutane-2-yl)carbamate
870487-09-5

tert-butyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentane-2-yl)amino)-3-methyl-1-oxobutane-2-yl)carbamate

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane / 3 h / 20 °C
2: sodium hydroxide; water / 1,4-dioxane / 3 h / 20 °C
View Scheme
Stage #1: tert-butyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentane-2-yl)amino)-3-methyl-1-oxobutane-2-yl)carbamate With trifluoroacetic acid In dichloromethane at 20℃; for 3h;
Stage #2: With water; sodium hydroxide In 1,4-dioxane at 20℃; for 3h;
Stage #1: tert-butyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentane-2-yl)amino)-3-methyl-1-oxobutane-2-yl)carbamate With trifluoroacetic acid In dichloromethane at 20℃; for 3h;
Stage #2: With water; sodium hydroxide In 1,4-dioxane at 20℃; for 3h;
tert-butyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentane-2-yl)amino)-3-methyl-1-oxobutane-2-yl)carbamate
870487-09-5

tert-butyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentane-2-yl)amino)-3-methyl-1-oxobutane-2-yl)carbamate

trifluoroacetic acid
76-05-1

trifluoroacetic acid

A

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

B

4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate

4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 3h;
In dichloromethane at 20℃; for 3h;
(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid

(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid

A

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

B

4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate

4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 16 h / 20 °C
2.1: diethylamine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: HATU / N,N-dimethyl-formamide / 1 h / 20 °C
3.2: 16 h / 20 °C
4.1: dichloromethane / 3 h / 20 °C
View Scheme
4-aminobenzenemethanol
623-04-1

4-aminobenzenemethanol

A

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

B

4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate

4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 16 h / 20 °C
2.1: diethylamine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: HATU / N,N-dimethyl-formamide / 1 h / 20 °C
3.2: 16 h / 20 °C
4.1: dichloromethane / 3 h / 20 °C
View Scheme
(9H-fluoren-9-yl)methyl (S)-(1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamate
870487-04-0

(9H-fluoren-9-yl)methyl (S)-(1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamate

A

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

B

4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate

4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: diethylamine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C
2.1: HATU / N,N-dimethyl-formamide / 1 h / 20 °C
2.2: 16 h / 20 °C
3.1: dichloromethane / 3 h / 20 °C
View Scheme
(S)-2-amino-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide
1037794-22-1

(S)-2-amino-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide

A

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

B

4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate

4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: HATU / N,N-dimethyl-formamide / 1 h / 20 °C
1.2: 16 h / 20 °C
2.1: dichloromethane / 3 h / 20 °C
View Scheme
C18H28N4O5

C18H28N4O5

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
2: N,N-dimethyl-formamide / 2 h / 30 °C
3: piperidine / N,N-dimethyl-formamide / 2 h / 30 °C
View Scheme
2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate
3496-11-5

2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 5 h / 20 °C
2: hydrogen; palladium 10% on activated carbon / dichloromethane; methanol / 5 h / 20 °C
View Scheme
C26H33N5O5

C26H33N5O5

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 20 °C / Darkness
2: triethylamine / N,N-dimethyl-formamide / 24 h / 20 °C
View Scheme
Nα-benzyloxy-carbonyl-L-citrulline
6692-89-3

Nα-benzyloxy-carbonyl-L-citrulline

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h / 20 °C
1.2: 48 h / 20 °C / Darkness
2.1: hydrogen; palladium 10% on activated carbon / dichloromethane; methanol / 5 h / 20 °C
3.1: N,N-dimethyl-formamide / 5 h / 20 °C
4.1: hydrogen; palladium 10% on activated carbon / dichloromethane; methanol / 5 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h / 20 °C
1.2: 48 h / 20 °C / Darkness
2.1: hydrogen; palladium 10% on activated carbon / dichloromethane; methanol / 5 h / 20 °C
3.1: piperidine / N,N-dimethyl-formamide / 20 h / 20 °C
4.1: triethylamine / N,N-dimethyl-formamide / 24 h / 20 °C
View Scheme
C21H26N4O5

C21H26N4O5

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen; palladium 10% on activated carbon / dichloromethane; methanol / 5 h / 20 °C
2: N,N-dimethyl-formamide / 5 h / 20 °C
3: hydrogen; palladium 10% on activated carbon / dichloromethane; methanol / 5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogen; palladium 10% on activated carbon / dichloromethane; methanol / 5 h / 20 °C
2: piperidine / N,N-dimethyl-formamide / 20 h / 20 °C
3: triethylamine / N,N-dimethyl-formamide / 24 h / 20 °C
View Scheme
N-Cbz-Val-Cit-4-aminobenzyl alcohol
159858-07-8

N-Cbz-Val-Cit-4-aminobenzyl alcohol

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol; dichloromethane at 20℃; for 5h;
tert-butyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentane-2-yl)amino)-3-methyl-1-oxobutane-2-yl)carbamate
870487-09-5

tert-butyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentane-2-yl)amino)-3-methyl-1-oxobutane-2-yl)carbamate

A

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

B

4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate

4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 3h;
L-valine
72-18-4

L-valine

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydrogencarbonate / water; 1,4-dioxane
1.2: 0 - 20 °C
2.1: dicyclohexyl-carbodiimide / tetrahydrofuran / 0 - 20 °C
3.1: sodium hydrogencarbonate / N,N-dimethyl-formamide; water; tetrahydrofuran / 20 °C
4.1: 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester / dichloromethane; methanol / 48 h / 20 °C / Darkness
5.1: diethylamine / N,N-dimethyl-formamide / 24 h
View Scheme
6-maleimidohexanoic acid N-hydroxylsuccinimide ester
55750-63-5

6-maleimidohexanoic acid N-hydroxylsuccinimide ester

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide
159857-80-4

6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one for 24h; Heating;100%
In 1-methyl-pyrrolidin-2-one at 20℃; for 24h;100%
In N,N-dimethyl-formamide at 20 - 30℃;97%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

2-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy)ethyl (4- nitrophenyl) carbonate

2-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy)ethyl (4- nitrophenyl) carbonate

C27H38N6O9

C27H38N6O9

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 2h;100%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Phth-PEG4-OSu
1415328-95-8

Phth-PEG4-OSu

C37H52N6O12
1415328-97-0

C37H52N6O12

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;98%
In N,N-dimethyl-formamide at 20℃;98%
In N,N-dimethyl-formamide at 20℃;98%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

C18H18N2O7
1415328-88-9

C18H18N2O7

C32H42N6O8
1415328-89-0

C32H42N6O8

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 24h;98%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

C23H28N2O10

C23H28N2O10

C37H52N6O12
1415328-97-0

C37H52N6O12

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;98%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

N-succinimidyl-6-maleimidohexanoate

N-succinimidyl-6-maleimidohexanoate

6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide
159857-80-4

6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 20℃; for 16h; Inert atmosphere;98%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

N2-acetyl-N6-(tert-butyloxycarbonyl)-L-lysine
23500-04-1

N2-acetyl-N6-(tert-butyloxycarbonyl)-L-lysine

N2-acetyl-N6-(tert-butoxycarbonyl)-L-lysyl-L-valyl-N5-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide

N2-acetyl-N6-(tert-butoxycarbonyl)-L-lysyl-L-valyl-N5-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.5h;97%
Stage #1: N2-acetyl-N6-(tert-butyloxycarbonyl)-L-lysine With HATU In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Cooling with ice;
Stage #2: (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Cooling with ice;
44%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

N2-acetyl-N6-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-lysine
148101-51-3

N2-acetyl-N6-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-lysine

N2-acetyl-N6-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-lysyl-L-valyl-N5-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide
1609108-48-6

N2-acetyl-N6-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-lysyl-L-valyl-N5-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere;95.6%
4-nitrophenyl 2-(2-(pyridin-2-yl)disulfanyl)ethyl carbonate
874302-76-8

4-nitrophenyl 2-(2-(pyridin-2-yl)disulfanyl)ethyl carbonate

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

2-(2-pyridyldisulfanyl)ethyl N-[(1S)-1-[[(1S)-1-[[4-(hydroxymethyl)phenyl]carbamoyl]-4-ureidobutyl]carbamoyl]-2-methylpropyl]carbamate

2-(2-pyridyldisulfanyl)ethyl N-[(1S)-1-[[(1S)-1-[[4-(hydroxymethyl)phenyl]carbamoyl]-4-ureidobutyl]carbamoyl]-2-methylpropyl]carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 16h; Inert atmosphere;95.4%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

pentafluorophenyl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate
692739-25-6

pentafluorophenyl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate

6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide
159857-80-4

6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;95%
N-Boc-6-aminohexanoic acid N-hydroxysuccinimide ester
51513-80-5

N-Boc-6-aminohexanoic acid N-hydroxysuccinimide ester

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Boc-Ahx-Val-Cit-PAB-OH

Boc-Ahx-Val-Cit-PAB-OH

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;94%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

4-azidobutanoic acid
54447-68-6

4-azidobutanoic acid

C22H34N8O5

C22H34N8O5

Conditions
ConditionsYield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In N,N-dimethyl-formamide at 20℃; for 5h;91%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

(1R,8S,9ξ)-bicyclo[6.1.0]non-4-yn-9-ylmethyl (4-nitrophenyl) carbonate

(1R,8S,9ξ)-bicyclo[6.1.0]non-4-yn-9-ylmethyl (4-nitrophenyl) carbonate

C29H41N5O6

C29H41N5O6

Conditions
ConditionsYield
With 4-methyl-morpholine In N,N-dimethyl-formamide at 23℃; for 24h;90%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid N-succinimidyl ester
64987-85-5

4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid N-succinimidyl ester

C30H42N6O7

C30H42N6O7

Conditions
ConditionsYield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In N,N-dimethyl-formamide at 20℃;89%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

8-oxononanoic acid
25542-64-7

8-oxononanoic acid

4-(N-(8-oxononanoyl)-L-valinyl-L-citrullinamido)benzyl alcohol

4-(N-(8-oxononanoyl)-L-valinyl-L-citrullinamido)benzyl alcohol

Conditions
ConditionsYield
Stage #1: 8-oxononanoic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at 20℃; for 0.666667h; Cooling with ice;
Stage #2: (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide In methanol; dichloromethane at 20℃;
88%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

C22H26N2O8

C22H26N2O8

C34H50N6O9

C34H50N6O9

Conditions
ConditionsYield
With triethylamine for 18h;88%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoic acid
88574-06-5

6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoic acid

N-(6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoyl)-L-valyl-N-5-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide
929259-98-3

N-(6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoyl)-L-valyl-N-5-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide

Conditions
ConditionsYield
Stage #1: 6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide In N,N-dimethyl-formamide for 15h;
82%
Stage #1: 6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere;
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

11-azido-3,6,9-trioxaundecanoic acid
172531-37-2

11-azido-3,6,9-trioxaundecanoic acid

C26H42N8O8

C26H42N8O8

Conditions
ConditionsYield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In N,N-dimethyl-formamide at 20℃; Inert atmosphere;82%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

N-acetyl-O-[1-(9H-fluoren-9-yl)-3-oxo-2,7,10,13,16,19-hexaoxa-4-azahenicosan-21-yl]-L-serine

N-acetyl-O-[1-(9H-fluoren-9-yl)-3-oxo-2,7,10,13,16,19-hexaoxa-4-azahenicosan-21-yl]-L-serine

N-acetyl-O-[1-(9H-fluoren-9-yl)-3-oxo-2,7,10,13,16,19-hexaoxa-4-azahenicosan-21-yl]-L-serylvalyl-N5-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide

N-acetyl-O-[1-(9H-fluoren-9-yl)-3-oxo-2,7,10,13,16,19-hexaoxa-4-azahenicosan-21-yl]-L-serylvalyl-N5-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 2h; Cooling with ice;80%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

2,5-dioxopyrrolidin-1-yl 2,5,8,11,14,17,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71-tetracosaoxatetraheptacontan-74-oate

2,5-dioxopyrrolidin-1-yl 2,5,8,11,14,17,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71-tetracosaoxatetraheptacontan-74-oate

C68H127N5O29

C68H127N5O29

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 16h;77%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

bis-(p-nitrophenyl) carbonate
5070-13-3

bis-(p-nitrophenyl) carbonate

C34H39N5O17S

C34H39N5O17S

C72H93N15O27S

C72H93N15O27S

Conditions
ConditionsYield
Stage #1: (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide; C34H39N5O17S With triethylamine In N,N-dimethyl-formamide for 3.5h;
Stage #2: bis-(p-nitrophenyl) carbonate With triethylamine In N,N-dimethyl-formamide for 1.25h;
70%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

but-3-yn-1-yl (4-nitrophenyl) carbonate

but-3-yn-1-yl (4-nitrophenyl) carbonate

but-3-yn-1-yl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate

but-3-yn-1-yl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate

Conditions
ConditionsYield
With 4-methyl-morpholine In N,N-dimethyl-formamide at 23℃; for 16h;66%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

N2-benzoyl-N6-(tert-butoxycarbonyl)-L-lysine

N2-benzoyl-N6-(tert-butoxycarbonyl)-L-lysine

N2-benzoyl-N6-(tert-butoxycarbonyl)-L-lysyl-L-valyl-N5-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide

N2-benzoyl-N6-(tert-butoxycarbonyl)-L-lysyl-L-valyl-N5-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 16h;63%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

C30H29NO8S2

C30H29NO8S2

C48H56N6O11S2

C48H56N6O11S2

Conditions
ConditionsYield
Stage #1: C30H29NO8S2 With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
62.2%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

3,6,9,12,15-pentaoxaoctadec-17-ynoic acid
1429934-37-1

3,6,9,12,15-pentaoxaoctadec-17-ynoic acid

C31H49N5O10

C31H49N5O10

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 12h;62%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

2,5-dioxopyrrolidin-1-yl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoate
64191-06-6

2,5-dioxopyrrolidin-1-yl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoate

C29H34N6O7

C29H34N6O7

Conditions
ConditionsYield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In N,N-dimethyl-formamide at 20℃;62%
(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide
159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oic acid

1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oic acid

1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca1(12),4(9),5,7,13,15-hexaen-10-yn-2-yl}-4-oxobutanamido)-N-[(1S)-1-{[(1S)-4-(carbamoylamino)-1-{[4-(hydroxymethyl)phenyl]carbamoyl}butyl]carbamoyl}-2-methylpropyl]-3,6,9,12-tetraoxapentadecan-15-amide

1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca1(12),4(9),5,7,13,15-hexaen-10-yn-2-yl}-4-oxobutanamido)-N-[(1S)-1-{[(1S)-4-(carbamoylamino)-1-{[4-(hydroxymethyl)phenyl]carbamoyl}butyl]carbamoyl}-2-methylpropyl]-3,6,9,12-tetraoxapentadecan-15-amide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 3h;60%
Stage #1: 1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide In N,N-dimethyl-formamide at 20℃; for 3h;
60%
Stage #1: 1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide In N,N-dimethyl-formamide at 20℃; for 3h;
60%
Stage #1: 1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide In N,N-dimethyl-formamide at 20℃; for 3h;
60%

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