(2S,4R)-4-hydroxy-1-(2-(3-methylisoxazol-5-yl)acetyl)-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

Base Information

• Chemical Name: (2S,4R)-4-hydroxy-1-(2-(3-methylisoxazol-5-yl)acetyl)-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
• CAS No.: 1418120-52-1
• Molecular Formula: C₂₂H₂₄N₄O₄S
• Molecular Weight: 440.523
• Mol file: 1418120-52-1.mol

Synonyms:(2S,4R)-4-hydroxy-1-(2-(3-methylisoxazol-5-yl)acetyl)-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

Chemical Property of (2S,4R)-4-hydroxy-1-(2-(3-methylisoxazol-5-yl)acetyl)-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-4-hydroxy-1-(2-(3-methylisoxazol-5-yl)acetyl)-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

There total 17 articles about (2S,4R)-4-hydroxy-1-(2-(3-methylisoxazol-5-yl)acetyl)-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide 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: 56.0%

(2S,4R)-4-(tert-butoxy)-1-(2-(3-methylisoxazol-5-yl)acetyl)-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (1448189-33-0) → (2S,4R)-4-hydroxy-1-(2-(3-methylisoxazol-5-yl)acetyl)-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (1418120-52-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 12h;

Reference yield: 43.0%

(2S,4R)-4-hydroxy-1-(2-(3-methylisoxazol-5-yl)acetyl)pyrrolidine-2-carboxylic acid (1448189-34-1) + 1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine (1448189-30-7) → (2S,4R)-4-hydroxy-1-(2-(3-methylisoxazol-5-yl)acetyl)-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (1418120-52-1)

Guidance literature:

(2S,4R)-4-hydroxy-1-(2-(3-methylisoxazol-5-yl)acetyl)pyrrolidine-2-carboxylic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h; Inert atmosphere;

1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1021/ml400296c

Reference yield:

4-bromobenzenecarbonitrile (623-00-7) → (2S,4R)-4-hydroxy-1-(2-(3-methylisoxazol-5-yl)acetyl)-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (1418120-52-1)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium acetate; palladium diacetate / N,N-dimethyl acetamide / 19 h / 150 °C / Inert atmosphere

2: cobalt(II) chloride; sodium tetrahydroborate / methanol / 0 - 4 °C

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 h / 4 - 20 °C

4: trifluoroacetic acid / dichloromethane / 12 h / 4 - 20 °C

With sodium tetrahydroborate; potassium acetate; palladium diacetate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; cobalt(II) chloride; In methanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide;

DOI:10.1002/anie.201206231

upstream raw materials:

2-(trimethylsilyl)ethyl 4-bromobenzylcarbamate

2-(trimethylsilyl)ethyl 4-(4-methylthiazol-5-yl)benzylcarbamate

1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine

4-bromobenzenecarbonitrile