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Moc-L-tert-Leucine
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Methoxycarbonyl-L-tert-leucine
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Methoxycarbonyl-L-tert-leucine
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162537-11-3 L-Valine,N-(methoxycarbonyl)-3-methyl-
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MethylCarbonylL-tertLeucine
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N-(Methoxycarbonyl)-L-tert-leucine
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Moc-L-Tert-Leucine
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162537-11-3 Usage

Chemical Properties

White Solid

References

Zhongmin Xu, †, et al. "Process Research and Development for an Efficient Synthesis of the HIV Protease Inhibitor BMS-232632." Organic Process Research & Development 6.3(2002):323-328.
Simhadri, Srinivas. "Process for the preparation of atazanavir bisulfate." (2016).
https://www.alfa.com/en/search/?q=14328-63-3

Description

Methoxycarbonyl-L-tert-leucine is a kind of amino acid deriviative. It is a very useful intermediate for efficient synthesis of the HIV protease inhibitor BMS-232632 as well as atazanavir bisulfate. 
InChI:InChI=1/C8H15NO4/c1-8(2,3)5(6(10)11)9-7(12)13-4/h5H,1-4H3,(H,9,12)(H,10,11)/t5-/m1/s1

162537-11-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
USP (1044356)  Atazanavir Related Compound A  United States Pharmacopeia (USP) Reference Standard 162537-11-3 1044356-25MG 14,500.98CNY Detail
Alfa Aesar (H35148)  N-Methoxycarbonyl-L-tert-leucine, 98%    162537-11-3 25g 5015.0CNY Detail
Alfa Aesar (H35148)  N-Methoxycarbonyl-L-tert-leucine, 98%    162537-11-3 5g 1252.0CNY Detail
Alfa Aesar (H35148)  N-Methoxycarbonyl-L-tert-leucine, 98%    162537-11-3 1g 312.0CNY Detail

162537-11-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Methoxycarbonyl-L-tert-leucine

1.2 Other means of identification

Product number -
Other names (S)-2-((Methoxycarbonyl)amino)-3,3-dimethylbutanoic 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:162537-11-3 SDS

162537-11-3Synthetic route

L-tert-Leucine
20859-02-3

L-tert-Leucine

methyl chloroformate
79-22-1

methyl chloroformate

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 60℃; for 18h; pH=8 - 9;100%
With sodium hydroxide In 1,4-dioxane; water at 25 - 60℃; for 22h;98%
Stage #1: L-tert-Leucine; methyl chloroformate With sodium hydroxide In 1,4-dioxane; water at 25 - 60℃; for 22h;
Stage #2: With hydrogenchloride In water
98%
N-tert-butyloxycarbonyl-L-tert-leucine
62965-35-9

N-tert-butyloxycarbonyl-L-tert-leucine

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / toluene; water / 3 h / 60 °C
2: sodium hydroxide / water / 2 h / 25 °C / pH 10 - 13
View Scheme
t-butoxycarbonylhydrazine
870-46-2

t-butoxycarbonylhydrazine

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

(S)-N'-(2-methoxycarbonylamino-3,3-dimethyl-butyryl)-hydrazinecarboxylic acid tert-butyl ester
198904-77-7

(S)-N'-(2-methoxycarbonylamino-3,3-dimethyl-butyryl)-hydrazinecarboxylic acid tert-butyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In ethyl acetate; N,N-dimethyl-formamide at 20℃; for 18.75h;100%
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With 4-methyl-morpholine; benzotriazol-1-ol for 0.5h; Inert atmosphere;
Stage #3: t-butoxycarbonylhydrazine at 20℃; for 20h; Inert atmosphere;
94%
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 25℃; for 0.25h;
Stage #2: t-butoxycarbonylhydrazine With 4-methyl-morpholine In DMF (N,N-dimethyl-formamide) at 25℃; for 16h;
90%
4-(5-bromo-pyridin-3-yloxymethyl)-pyrrolidine-2-carboxylic acid methyl ester
630424-01-0

4-(5-bromo-pyridin-3-yloxymethyl)-pyrrolidine-2-carboxylic acid methyl ester

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

4-(5-bromo-pyridin-3-yloxymethyl)-1-(2-methoxycarbonylamino-3,3-dimethyl-butyryl)-pyrrolidine-2-carboxylic acid methyl ester
630424-03-2

4-(5-bromo-pyridin-3-yloxymethyl)-1-(2-methoxycarbonylamino-3,3-dimethyl-butyryl)-pyrrolidine-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃;100%
methyl [(S)-1-{[(2S,3S,5S)-5-{[(tert-butoxy)carbonyl]amino}-3-hydroxy-6-phenyl-1-[4-(quinolin-3-yl)phenyl]hexan-2-yl]amino}-3,3-dimethyl-1-oxobutan]-2-ylcarbamate
1335054-61-9

methyl [(S)-1-{[(2S,3S,5S)-5-{[(tert-butoxy)carbonyl]amino}-3-hydroxy-6-phenyl-1-[4-(quinolin-3-yl)phenyl]hexan-2-yl]amino}-3,3-dimethyl-1-oxobutan]-2-ylcarbamate

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

dimethyl (2S,2'S)-1,1'-((2S,3S,5S)-3-hydroxy-6-benzyl-1-(4-(quinolin-3-yl)phenyl)hexane-2,5-diyl)bis(azanediyl)bis(3,3-dimethyl-1-oxobutane-2,1-diyl)dicarbamate
1335054-35-7

dimethyl (2S,2'S)-1,1'-((2S,3S,5S)-3-hydroxy-6-benzyl-1-(4-(quinolin-3-yl)phenyl)hexane-2,5-diyl)bis(azanediyl)bis(3,3-dimethyl-1-oxobutane-2,1-diyl)dicarbamate

Conditions
ConditionsYield
Stage #1: methyl [(S)-1-{[(2S,3S,5S)-5-{[(tert-butoxy)carbonyl]amino}-3-hydroxy-6-phenyl-1-[4-(quinolin-3-yl)phenyl]hexan-2-yl]amino}-3,3-dimethyl-1-oxobutan]-2-ylcarbamate With hydrogenchloride In 1,4-dioxane at 20℃; for 0.5h; Inert atmosphere;
Stage #2: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one at 20℃; for 16h; Inert atmosphere;
100%
C29H33FN2O4S
1311412-52-8

C29H33FN2O4S

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

C32H38FN3O5S
1311412-53-9

C32H38FN3O5S

Conditions
ConditionsYield
Stage #1: C29H33FN2O4S With hydrogenchloride In 1,4-dioxane at 20℃; for 1h;
Stage #2: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 0 - 20℃; for 3h;
96%
{(S)-1-[N'-((2S,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester
857900-54-0

{(S)-1-[N'-((2S,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-N'-(4-pyridin-2-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl ester

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane95%
1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-(5S)-2,5-diamino-6-phenyl-2-azahexane

1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-(5S)-2,5-diamino-6-phenyl-2-azahexane

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
With pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 35℃; for 1.5h; Temperature; Concentration;91.6%
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane
156732-15-9

(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

methyl ((S)-1-(((2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl)amino)-3,3-dimethyl-1-oxobutan-2-yl)carbamate

methyl ((S)-1-(((2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl)amino)-3,3-dimethyl-1-oxobutan-2-yl)carbamate

Conditions
ConditionsYield
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 0 - 20℃; for 4h;87%
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0℃; for 0.25h;
Stage #2: (2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 24h; Further stages.;
N-[4-(2-pyridyl)phenylmethylidene]hydrazine
257907-05-4

N-[4-(2-pyridyl)phenylmethylidene]hydrazine

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

(S)-[2,2-dimethyl-1-(4-pyridin-2-yl-benzylidene-hydrazinocarbonyl)-propyl]-carbamic acid methyl ester
1003888-24-1

(S)-[2,2-dimethyl-1-(4-pyridin-2-yl-benzylidene-hydrazinocarbonyl)-propyl]-carbamic acid methyl ester

Conditions
ConditionsYield
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -30 - -25℃;
Stage #2: N-[4-(2-pyridyl)phenylmethylidene]hydrazine In dichloromethane at -25 - 20℃; for 2.5h;
85%
bis(1,1-dimethylethyl) (2S,2'S)-2,2'-[benzene-1,4-diylbis(1H-benzimidazole-5,2-diyl)]di(1-pyrrolidinecarboxylate)
1239649-51-4

bis(1,1-dimethylethyl) (2S,2'S)-2,2'-[benzene-1,4-diylbis(1H-benzimidazole-5,2-diyl)]di(1-pyrrolidinecarboxylate)

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

dimethyl (benzene-1,4-diylbis{1H-benzimidazole-5,2-diyl(2S)-2,1-pyrrolidinediyl[(2S)-3,3-dimethyl-1-oxo-1,2-butanediyl]})biscarbamate
1239653-22-5

dimethyl (benzene-1,4-diylbis{1H-benzimidazole-5,2-diyl(2S)-2,1-pyrrolidinediyl[(2S)-3,3-dimethyl-1-oxo-1,2-butanediyl]})biscarbamate

Conditions
ConditionsYield
Stage #1: bis(1,1-dimethylethyl) (2S,2'S)-2,2'-[benzene-1,4-diylbis(1H-benzimidazole-5,2-diyl)]di(1-pyrrolidinecarboxylate) With hydrogenchloride In 1,4-dioxane at 20℃; for 0.5h;
Stage #2: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 2h;
85%
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride

1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
With 4-methyl-morpholine; diisopropyl-carbodiimide In dichloromethane; isopropyl alcohol at -10 - 20℃; Product distribution / selectivity; Inert atmosphere;84%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 22 - 25℃; Reagent/catalyst; Large scale;82.1%
With O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine 1.) CH2Cl2, 0 deg C, 20 min, 2.) CH2Cl2, overnight; Yield given. Multistep reaction;
[5-(1-cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl]-carbamic acid 9H-fluoren-9-ylmethyl ester hydrochloride
919094-63-6

[5-(1-cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl]-carbamic acid 9H-fluoren-9-ylmethyl ester hydrochloride

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

C37H45N5O9S
919094-46-5

C37H45N5O9S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) In acetonitrile at 20℃;82%
methyl (S)-1-((2R,4S,5S)-5-amino-4-hydroxy-6-phenyl-1-(4-(pyridin-2-yl)phenyl)hexan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate
854754-00-0

methyl (S)-1-((2R,4S,5S)-5-amino-4-hydroxy-6-phenyl-1-(4-(pyridin-2-yl)phenyl)hexan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

methyl (1S,4R,6S,7S,10S)-7-benzyl-1,10-ditert-butyl-6-hydroxy-2,9,12-trioxo-4-[4-(2-pyridinyl)benzyl]-13-oxa-3,8,11-triazatetradec-1-ylcarbamate

methyl (1S,4R,6S,7S,10S)-7-benzyl-1,10-ditert-butyl-6-hydroxy-2,9,12-trioxo-4-[4-(2-pyridinyl)benzyl]-13-oxa-3,8,11-triazatetradec-1-ylcarbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran at 25℃; for 16h;81%
methyl (S)-1-((2R,4S,5S)-5-amino-4-hydroxy-6-phenyl-1-(4-(pyridin-2-yl)phenyl)hexan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate
854754-00-0

methyl (S)-1-((2R,4S,5S)-5-amino-4-hydroxy-6-phenyl-1-(4-(pyridin-2-yl)phenyl)hexan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

methyl (1S,4R,6S,7S,10S)-7-benzyl-1,10-ditert-butyl-6-hydroxy-2,9,12-trioxo-4-[4-(2-pyridinyl)benzyl]-13-oxa-3,8,11-triazatetradec-1-ylcarbamate

methyl (1S,4R,6S,7S,10S)-7-benzyl-1,10-ditert-butyl-6-hydroxy-2,9,12-trioxo-4-[4-(2-pyridinyl)benzyl]-13-oxa-3,8,11-triazatetradec-1-ylcarbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran at 25℃; for 16h;81%
(S)-2-amino-1-phenyl-but-3-ene hydrochloride

(S)-2-amino-1-phenyl-but-3-ene hydrochloride

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

(3S)-3-{[N-(methoxycarbonyl)-L-tert-leucinyl]amino}-4-phenyl-1-butene
1192510-21-6

(3S)-3-{[N-(methoxycarbonyl)-L-tert-leucinyl]amino}-4-phenyl-1-butene

Conditions
ConditionsYield
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -25 - -22℃;
Stage #2: (S)-2-amino-1-phenyl-but-3-ene hydrochloride In dichloromethane at 20℃; for 2h;
81%
C33H45N5O4S

C33H45N5O4S

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

methyl (1S)-1-{[((1S,3S,4S)-1-benzyl-3-hydroxy-4-{[(2S)-2-(3-{[2-(methoxymethyl)-1,3-thiazol-4-yl]methyl}-2-oxo-1-imidazolidinyl)-3,3-dimethylbutanoyl]amino}-5-phenylpentyl)amino]carbonyl}-2,2-dimethylpropylcarbamate

methyl (1S)-1-{[((1S,3S,4S)-1-benzyl-3-hydroxy-4-{[(2S)-2-(3-{[2-(methoxymethyl)-1,3-thiazol-4-yl]methyl}-2-oxo-1-imidazolidinyl)-3,3-dimethylbutanoyl]amino}-5-phenylpentyl)amino]carbonyl}-2,2-dimethylpropylcarbamate

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 0 - 25℃; for 16h;79%
Stage #1: C33H45N5O4S; (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 0 - 25℃; for 16h;
Stage #2: With citric acid In water; ethyl acetate
79%
C33H36FN3O4S
1311412-03-9

C33H36FN3O4S

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

C41H49FN4O7S
1311410-69-1

C41H49FN4O7S

Conditions
ConditionsYield
With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h;79%
With triethylamine; HATU In N,N-dimethyl-formamide at 20℃;
With triethylamine; HATU In N,N-dimethyl-formamide at 25 - 30℃; for 0.5h;26.97 g
(2S)-N-{(1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-[4-(6-methyl-3-pyridinyl)phenyl]pentyl}-3,3-dimethyl-2-{3-[(6-methyl-2-pyridinyl)methyl]-2-oxo-1-imidazolidinyl}butanamide hydrochloride

(2S)-N-{(1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-[4-(6-methyl-3-pyridinyl)phenyl]pentyl}-3,3-dimethyl-2-{3-[(6-methyl-2-pyridinyl)methyl]-2-oxo-1-imidazolidinyl}butanamide hydrochloride

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

methyl (1S)-1-[({(1S,2S,4S)-4-[((2S)-3,3-dimethyl-2-{3-[(6-methyl-2-pyridinyl)methyl]-2-oxo-1-imidazolidinyl}butanoyl)amino]-2-hydroxy-1-[4-(6-methyl-3-pyridinyl)benzyl]-5-phenylpentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate

methyl (1S)-1-[({(1S,2S,4S)-4-[((2S)-3,3-dimethyl-2-{3-[(6-methyl-2-pyridinyl)methyl]-2-oxo-1-imidazolidinyl}butanoyl)amino]-2-hydroxy-1-[4-(6-methyl-3-pyridinyl)benzyl]-5-phenylpentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran at 25℃; for 16h;77%
With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran at 25℃; for 16h;77%
(2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane
144163-85-9

(2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

methyl (1S)-1-[({(1S,2S,4S)-1-benzyl-4-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-phenylpentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate
854754-32-8

methyl (1S)-1-[({(1S,2S,4S)-1-benzyl-4-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-phenylpentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate

Conditions
ConditionsYield
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 25℃; for 1h;
Stage #2: (2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane In DMF (N,N-dimethyl-formamide) at 25℃; for 16h;
77%
(4-bromobenzyl)hydrazine dihydrochloride

(4-bromobenzyl)hydrazine dihydrochloride

1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride
25952-53-8

1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

{(1S)-1-[N'-(4-bromobenzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}carbamic acid methyl ester
872703-59-8

{(1S)-1-[N'-(4-bromobenzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}carbamic acid methyl ester

Conditions
ConditionsYield
Stage #1: (4-bromobenzyl)hydrazine dihydrochloride; (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With 4-methyl-morpholine; benzotriazol-1-ol In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; for 15h; Inert atmosphere;
77%
3-bromobenzylhydrazine

3-bromobenzylhydrazine

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

{(1S)-1-[N'-(3-bromo-benzyl)hydrazinocarbonyl]-2,2-dimethyl-propyl}carbamic acid methyl ester
882435-39-4

{(1S)-1-[N'-(3-bromo-benzyl)hydrazinocarbonyl]-2,2-dimethyl-propyl}carbamic acid methyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In ethyl acetate at 20℃;76%
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In ethyl acetate at 20℃;76%
tert-butyl (1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate hydrochloride

tert-butyl (1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate hydrochloride

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

methyl (S)-1-((2S,4S,5S)-5-(tert-butoxycarbonyl)amino-4-hydroxy-6-phenyl-1-(4-(pyridin-2-yl)phenyl)hexan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

methyl (S)-1-((2S,4S,5S)-5-(tert-butoxycarbonyl)amino-4-hydroxy-6-phenyl-1-(4-(pyridin-2-yl)phenyl)hexan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran at 25℃; for 16h;75%
methyl (S)-1-((2S,4S,5S)-5-amino-4-hydroxy-6-phenyl-1-(4-(pyridin-2-yl)phenyl)hexan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate
854754-04-4

methyl (S)-1-((2S,4S,5S)-5-amino-4-hydroxy-6-phenyl-1-(4-(pyridin-2-yl)phenyl)hexan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

dimethyl (2S,2'S)-1,1'-((2S,3S,5S)-3-hydroxy-1-phenyl-6-(4-(pyridin-2-yl)phenyl)hexane-2,5-diyl)bis(azanediyl)bis(3,3-dimethyl-1-oxobutane-2,1-diyl)dicarbamate

dimethyl (2S,2'S)-1,1'-((2S,3S,5S)-3-hydroxy-1-phenyl-6-(4-(pyridin-2-yl)phenyl)hexane-2,5-diyl)bis(azanediyl)bis(3,3-dimethyl-1-oxobutane-2,1-diyl)dicarbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran at 25℃; for 3h;75%
With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran at 25℃; for 3h;75%
With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;75%
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane
437713-06-9

1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane

atazanavir
198904-31-3

atazanavir

Conditions
ConditionsYield
Stage #1: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With thionyl chloride; triethylamine In dichloromethane at 42℃; for 3h;
Stage #2: 1-[4-(pyridine-2-yl)phenyl]-(5S)-2,5-diamino-(4S)-hydroxy-6-phenyl-2-azahexane In dichloromethane at 20℃; Solvent; Temperature; Concentration;
74.2%
tert-butyl (1S,2S,4R)-4-amino-1-benzyl-2-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate hydrochloride salt

tert-butyl (1S,2S,4R)-4-amino-1-benzyl-2-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate hydrochloride salt

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

methyl (S)-1-((2R,4S,5S)-5-(tert-butoxycarbonyl)amino-4-hydroxy-6-phenyl-1-(4-(pyridin-2-yl)phenyl)hexan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

methyl (S)-1-((2R,4S,5S)-5-(tert-butoxycarbonyl)amino-4-hydroxy-6-phenyl-1-(4-(pyridin-2-yl)phenyl)hexan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran at 25℃; for 16h;74%
With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran at 25℃; for 16h;74%
(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

(2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane
144164-11-4

(2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane

N1-((1S,3S,4S)-1-benzyl-3-hydroxy-5-phenyl-4-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}pentyl)-N2-(methoxycarbonyl)-3-methyl-L-valinamide

N1-((1S,3S,4S)-1-benzyl-3-hydroxy-5-phenyl-4-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}pentyl)-N2-(methoxycarbonyl)-3-methyl-L-valinamide

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;73.5%
methyl (1S)-1-[({(1S,3S,4S)-4-amino-3-hydroxy-1-[4-(5-methyl-2-pyridinyl)benzyl]-5-phenylpentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate
854757-30-5

methyl (1S)-1-[({(1S,3S,4S)-4-amino-3-hydroxy-1-[4-(5-methyl-2-pyridinyl)benzyl]-5-phenylpentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

methyl (1S,4S,5S,7S,10S)-4-benzyl-1,10-ditert-butyl-5-hydroxy-7-[4-(5-methyl-2-pyridinyl)benzyl]-2,9,12-trioxo-13-oxa-3,8,11-triazatetradec-1-ylcarbamate

methyl (1S,4S,5S,7S,10S)-4-benzyl-1,10-ditert-butyl-5-hydroxy-7-[4-(5-methyl-2-pyridinyl)benzyl]-2,9,12-trioxo-13-oxa-3,8,11-triazatetradec-1-ylcarbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran at 25℃; for 72h;73%
With N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran at 25℃; for 72h;73%
di-tert-butyl 2,2'-(((sulfonylbis(oxy))bis(3,1-phenylene))bis(1H-imidazole-5,2-diyl))(2S,2'S)-bis(pyrrolidine-1-carboxylate)

di-tert-butyl 2,2'-(((sulfonylbis(oxy))bis(3,1-phenylene))bis(1H-imidazole-5,2-diyl))(2S,2'S)-bis(pyrrolidine-1-carboxylate)

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

bis(3-(2-((S)-1-((R)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl)pyrrolidine-2-yl)-1H-imidazol-5-yl)phenyl)sulfate

bis(3-(2-((S)-1-((R)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl)pyrrolidine-2-yl)-1H-imidazol-5-yl)phenyl)sulfate

Conditions
ConditionsYield
Stage #1: di-tert-butyl 2,2'-(((sulfonylbis(oxy))bis(3,1-phenylene))bis(1H-imidazole-5,2-diyl))(2S,2'S)-bis(pyrrolidine-1-carboxylate) With trifluoroacetic acid In dichloromethane at 20℃; for 0.5h;
Stage #2: (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;
73%
(2S,3S)-N-((1S,2S)-1-benzyl-2-hydroxy-3-{1-[4-(2-pyridinyl)benzyl]hydrazino}propyl)-3-methyl-2-[2-oxo-3-(4-quinolinylmethyl)-1-imidazolidinyl]pentanamide
857904-38-2

(2S,3S)-N-((1S,2S)-1-benzyl-2-hydroxy-3-{1-[4-(2-pyridinyl)benzyl]hydrazino}propyl)-3-methyl-2-[2-oxo-3-(4-quinolinylmethyl)-1-imidazolidinyl]pentanamide

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid
162537-11-3

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid

tert-butyl (1S)-1-({2-[(2S,3S)-2-hydroxy-3-({(2S,3S)-3-methyl-2-[2-oxo-3-(4-quinolinylmethyl)-1-imidazolidinyl]pentanoyl}amino)-4-phenylbutyl]-2-[4-(2-pyridinyl)benzyl]hydrazino}carbonyl)-2,2-dimethylpropylcarbamate

tert-butyl (1S)-1-({2-[(2S,3S)-2-hydroxy-3-({(2S,3S)-3-methyl-2-[2-oxo-3-(4-quinolinylmethyl)-1-imidazolidinyl]pentanoyl}amino)-4-phenylbutyl]-2-[4-(2-pyridinyl)benzyl]hydrazino}carbonyl)-2,2-dimethylpropylcarbamate

Conditions
ConditionsYield
Stage #1: (2S,3S)-N-((1S,2S)-1-benzyl-2-hydroxy-3-{1-[4-(2-pyridinyl)benzyl]hydrazino}propyl)-3-methyl-2-[2-oxo-3-(4-quinolinylmethyl)-1-imidazolidinyl]pentanamide; (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid With triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one In tetrahydrofuran; DMF (N,N-dimethyl-formamide) at 25℃; for 4h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate for 0.5h;
72%

162537-11-3Downstream Products

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