4-Thiazolidinecarboxamide, 3-[(2S,3S)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]-N-(1,1-dimethylethyl )-5,5-dimethyl-, (4R)-

Base Information

• Chemical Name: 4-Thiazolidinecarboxamide, 3-[(2S,3S)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]-N-(1,1-dimethylethyl )-5,5-dimethyl-, (4R)-
• CAS No.: 184955-18-8
• Molecular Formula: C20H31N3O3S
• Molecular Weight: 393.55
• Mol file: 184955-18-8.mol

Synonyms:

Chemical Property of 4-Thiazolidinecarboxamide, 3-[(2S,3S)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]-N-(1,1-dimethylethyl )-5,5-dimethyl-, (4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Thiazolidinecarboxamide, 3-[(2S,3S)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]-N-(1,1-dimethylethyl )-5,5-dimethyl-, (4R)-

There total 8 articles about 4-Thiazolidinecarboxamide, 3-[(2S,3S)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]-N-(1,1-dimethylethyl )-5,5-dimethyl-, (4R)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Boc-Apns-Dmt-NHtBu (159000-71-2) → (R)-N-tert-butyl-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-5,5-dimethyl-1,3-thiazolidine-4-carboxamide (184955-18-8)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane;

DOI:10.1002/(SICI)1521-4184(199803)331:3<87::AID-ARDP87>3.0.CO;2-H

Reference yield:

(R)-N-tert-butyl-5,5-dimethyl-1,3-thiazolidine-4-carboxamide (158941-58-3) → (R)-N-tert-butyl-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-5,5-dimethyl-1,3-thiazolidine-4-carboxamide (184955-18-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 7.97 g / EDC*HCl; HOBt; Et₃N / dimethylformamide / 20 °C

2: 4 N HCl / dioxane / 2 h / 20 °C

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(02)00322-X

Reference yield:

(R)-4-tert-Butylcarbamoyl-5,5-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester (148983-13-5) → (R)-N-tert-butyl-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-5,5-dimethyl-1,3-thiazolidine-4-carboxamide (184955-18-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 4 N HCl / dioxane / 2 h / 20 °C

2: 7.97 g / EDC*HCl; HOBt; Et₃N / dimethylformamide / 20 °C

3: 4 N HCl / dioxane / 2 h / 20 °C

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(02)00322-X

upstream raw materials:

Boc-Apns-Dmt-NHtBu

(2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid

(R)-N-tert-butyl-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

(R)-4-tert-Butylcarbamoyl-5,5-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

KNI-727

Acetic acid 3-[(1S,2S)-1-benzyl-3-((R)-4-tert-butylcarbamoyl-5,5-dimethyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propylcarbamoyl]-2-ethyl-phenyl ester

(R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)amino-3-methylbutanoyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

(R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)aminosuccinamyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide