2-S-{[(3-benzyloxycarbonyl-3-R-methanesulfanyl-propanoyl-amino)methyl]carbamoyl}pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: 2-S-{[(3-benzyloxycarbonyl-3-R-methanesulfanyl-propanoyl-amino)methyl]carbamoyl}pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 374756-30-6
• Molecular Formula: C₂₆H₃₁N₃O₆S
• Molecular Weight: 513.615
• Mol file: 374756-30-6.mol

Synonyms:2-S-{[(3-benzyloxycarbonyl-3-R-methanesulfanyl-propanoyl-amino)methyl]carbamoyl}pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property of 2-S-{[(3-benzyloxycarbonyl-3-R-methanesulfanyl-propanoyl-amino)methyl]carbamoyl}pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-S-{[(3-benzyloxycarbonyl-3-R-methanesulfanyl-propanoyl-amino)methyl]carbamoyl}pyrrolidine-1-carboxylic acid benzyl ester

There total 5 articles about 2-S-{[(3-benzyloxycarbonyl-3-R-methanesulfanyl-propanoyl-amino)methyl]carbamoyl}pyrrolidine-1-carboxylic acid benzyl 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: 70.0%

(2R)-methanesulfanyl-succinic acid 1-benzyl ester (260408-11-5) + [2-S-(aminomethyl-carbamoyl)pyrrolidine]-1-carbamic acid benzyl ester hydrochloride → 2-S-{[(3-benzyloxycarbonyl-3-R-methanesulfanyl-propanoyl-amino)methyl]carbamoyl}pyrrolidine-1-carboxylic acid benzyl ester (374756-30-6)

Guidance literature:

With N-ethylmorpholine;; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ja003770j

Reference yield:

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid (66178-04-9) → 2-S-{[(3-benzyloxycarbonyl-3-R-methanesulfanyl-propanoyl-amino)methyl]carbamoyl}pyrrolidine-1-carboxylic acid benzyl ester (374756-30-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: K₃CO₃ / dimethylformamide / 96 h / 20 °C

2.1: 2,6-lutidine; triflic anhydride / CH₂Cl₂ / 4 h / -78 °C

2.2: 15-crown-5 / CH₂Cl₂; dimethylformamide / -78 - 20 °C

3.1: TFA / CH₂Cl₂ / 0 °C

4.1: 70 percent / EDAC; HOBT; N-ethylmorpholine / CH₂Cl₂ / 1 h / 0 °C

With N-ethylmorpholine;; 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja003770j

Reference yield:

(2S)-hydroxysuccinic acid-1-benzyl ester-4-(4-methoxybenzyl) ester (260408-09-1) → 2-S-{[(3-benzyloxycarbonyl-3-R-methanesulfanyl-propanoyl-amino)methyl]carbamoyl}pyrrolidine-1-carboxylic acid benzyl ester (374756-30-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,6-lutidine; triflic anhydride / CH₂Cl₂ / 4 h / -78 °C

1.2: 15-crown-5 / CH₂Cl₂; dimethylformamide / -78 - 20 °C

2.1: TFA / CH₂Cl₂ / 0 °C

3.1: 70 percent / EDAC; HOBT; N-ethylmorpholine / CH₂Cl₂ / 1 h / 0 °C

With N-ethylmorpholine;; 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja003770j

upstream raw materials:

(2R)-methanesulfanyl-succinic acid 1-benzyl ester

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid

(2S)-hydroxysuccinic acid-1-benzyl ester-4-(4-methoxybenzyl) ester

(2R)-methanesulfanyl-succinic acid-1-benzyl ester-4-(4-methoxybenzyl) ester