(2S,4S,5R)-4-(aminocarbonyl)-1-(3-methoxy-4-tert-butylbenzoyl)-2-isobutyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,4S,5R)-4-(aminocarbonyl)-1-(3-methoxy-4-tert-butylbenzoyl)-2-isobutyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester
• CAS No.: 927436-31-5
• Molecular Formula: C₂₉H₄₁N₃O₅S
• Molecular Weight: 543.728
• Mol file: 927436-31-5.mol

Synonyms:(2S,4S,5R)-4-(aminocarbonyl)-1-(3-methoxy-4-tert-butylbenzoyl)-2-isobutyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Chemical Property of (2S,4S,5R)-4-(aminocarbonyl)-1-(3-methoxy-4-tert-butylbenzoyl)-2-isobutyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5R)-4-(aminocarbonyl)-1-(3-methoxy-4-tert-butylbenzoyl)-2-isobutyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester

There total 4 articles about (2S,4S,5R)-4-(aminocarbonyl)-1-(3-methoxy-4-tert-butylbenzoyl)-2-isobutyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester 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: 66.0%

(2S,4S,5R)-4-(aminocarbonyl)-2-isobutyl-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid tert-butyl ester (927436-23-5) + 3-methoxy-4-tert-butylbenzoyl chloride (35291-92-0) → (2S,4S,5R)-4-(aminocarbonyl)-1-(3-methoxy-4-tert-butylbenzoyl)-2-isobutyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester (927436-31-5)

Guidance literature:

With triethylamine; In dichloromethane; for 18h; Heating;

DOI:10.1021/jm061207r

Reference yield:

2-[N-(1,3-thiazol-2-ylmethylene)amino]-4-methylpentanoic acid tert-butyl ester (521955-41-9) → (2S,4S,5R)-4-(aminocarbonyl)-1-(3-methoxy-4-tert-butylbenzoyl)-2-isobutyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester (927436-31-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / lithium bromide; triethylamine / tetrahydrofuran / 21 h / 20 °C

2: 432 mg / (-)-di-O,O'-p-tolyl-L-tartaric acid / CH₂Cl₂ / 20 °C

3: 66 percent / triethylamine / CH₂Cl₂ / 18 h / Heating

With (-)-di-O,O'-p-tolyl-L-tartaric acid; triethylamine; lithium bromide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm061207r

Reference yield:

rac-(2S,4S,5R)-4-(aminocarbonyl)-2-isobutyl-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid tert-butyl ester → (2S,4S,5R)-4-(aminocarbonyl)-1-(3-methoxy-4-tert-butylbenzoyl)-2-isobutyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester (927436-31-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 432 mg / (-)-di-O,O'-p-tolyl-L-tartaric acid / CH₂Cl₂ / 20 °C

2: 66 percent / triethylamine / CH₂Cl₂ / 18 h / Heating

With (-)-di-O,O'-p-tolyl-L-tartaric acid; triethylamine; In dichloromethane;

DOI:10.1021/jm061207r

upstream raw materials:

(2S,4S,5R)-4-(aminocarbonyl)-2-isobutyl-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid tert-butyl ester

3-methoxy-4-tert-butylbenzoyl chloride

2-[N-(1,3-thiazol-2-ylmethylene)amino]-4-methylpentanoic acid tert-butyl ester

leucine tert-butyl ester hydrochloride