3-((2S,4S)-1-tert-butoxycarbonyl-4-(4-chlorophenyl)amino-2-pyrrolidinylcarbonyl)-1,3-thiazolidine

Base Information

• Chemical Name: 3-((2S,4S)-1-tert-butoxycarbonyl-4-(4-chlorophenyl)amino-2-pyrrolidinylcarbonyl)-1,3-thiazolidine
• CAS No.: 401565-11-5
• Molecular Formula: C₁₉H₂₆ClN₃O₃S
• Molecular Weight: 411.953
• Mol file: 401565-11-5.mol

Synonyms:3-((2S,4S)-1-tert-butoxycarbonyl-4-(4-chlorophenyl)amino-2-pyrrolidinylcarbonyl)-1,3-thiazolidine

Chemical Property of 3-((2S,4S)-1-tert-butoxycarbonyl-4-(4-chlorophenyl)amino-2-pyrrolidinylcarbonyl)-1,3-thiazolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((2S,4S)-1-tert-butoxycarbonyl-4-(4-chlorophenyl)amino-2-pyrrolidinylcarbonyl)-1,3-thiazolidine

There total 4 articles about 3-((2S,4S)-1-tert-butoxycarbonyl-4-(4-chlorophenyl)amino-2-pyrrolidinylcarbonyl)-1,3-thiazolidine 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: 67.0%

(2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester (401564-36-1) + 4-chloro-aniline (106-47-8) → 3-((2S,4S)-1-tert-butoxycarbonyl-4-(4-chlorophenyl)amino-2-pyrrolidinylcarbonyl)-1,3-thiazolidine (401565-11-5)

Guidance literature:

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2006.01.022

Reference yield:

3-[(2S,4R)-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinylcarbonyl]-1,3-thiazolidine (401564-30-5) → 3-((2S,4S)-1-tert-butoxycarbonyl-4-(4-chlorophenyl)amino-2-pyrrolidinylcarbonyl)-1,3-thiazolidine (401565-11-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 30.3 g / sulfur trioxide pyridine complex; triethylamine / CH₂Cl₂; dimethylsulfoxide / 2 h

2: 67 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 3 h / 20 °C

With sulfur trioxide pyridine complex; sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane;

DOI:10.1016/j.bmc.2006.01.022

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → 3-((2S,4S)-1-tert-butoxycarbonyl-4-(4-chlorophenyl)amino-2-pyrrolidinylcarbonyl)-1,3-thiazolidine (401565-11-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 3-hydroxybenzotriazole hydrate; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide / 18 h / 20 °C

2: 30.3 g / sulfur trioxide pyridine complex; triethylamine / CH₂Cl₂; dimethylsulfoxide / 2 h

3: 67 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 3 h / 20 °C

With sulfur trioxide pyridine complex; sodium tris(acetoxy)borohydride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.01.022

upstream raw materials:

(2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester

4-chloro-aniline

3-[(2S,4R)-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinylcarbonyl]-1,3-thiazolidine

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid