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

Base Information

• Chemical Name: (2S,4R)-4-(tert-butoxy)-1-(2-(3-methylisoxazol-5-yl)acetyl)-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
• CAS No.: 1448189-33-0
• Molecular Formula: C₂₆H₃₂N₄O₄S
• Molecular Weight: 496.63
• Mol file: 1448189-33-0.mol

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

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

There total 10 articles about (2S,4R)-4-(tert-butoxy)-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: 88.0%

(2S,4R)-4-(tert-butoxy)-1-(2-(3-methylisoxazol-5-yl)acetyl)pyrrolidine-2-carboxylic acid (1448189-32-9) + 1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine (1448189-30-7) → (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)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 4 - 20 ℃; for 20h;

DOI:10.1002/anie.201206231

Reference yield:

2-(trimethylsilyl)ethyl 4-(4-methylthiazol-5-yl)benzylcarbamate (1448189-29-4) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / acetonitrile / 24 h / 20 °C

2: 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

With tetrabutyl ammonium fluoride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/anie.201206231

Reference yield:

2-(trimethylsilyl)ethyl 4-bromobenzylcarbamate (1448189-28-3) → (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)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutyl-ammonium chloride; bis(tri-tert-butylphosphine)palladium⁽⁰⁾; caesium carbonate / N,N-dimethyl-formamide / 0.13 h / 170 °C / Microwave irradiation

2: tetrabutyl ammonium fluoride / acetonitrile / 24 h / 20 °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

With bis(tri-tert-butylphosphine)palladium⁽⁰⁾; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; benzotriazol-1-ol; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/anie.201206231

upstream raw materials:

(2S,4R)-4-(tert-butoxy)-1-(2-(3-methylisoxazol-5-yl)acetyl)pyrrolidine-2-carboxylic acid

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

2-(trimethylsilyl)ethyl 4-bromobenzylcarbamate

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

Downstream raw materials:

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

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