cis-4-Phenylthio-L-proline hydrochloride

Base Information

• Chemical Name: cis-4-Phenylthio-L-proline hydrochloride
• CAS No.: 105107-84-4
• Molecular Formula: C11H14ClNO2S
• Molecular Weight: 259.757
• Mol file: 105107-84-4.mol

Synonyms:L-Proline,4-(phenylthio)-, hydrochloride, (4S)- (9CI);L-Proline, 4-(phenylthio)-,hydrochloride, cis-;(4S)-4-(Phenylthio)-L-proline hydrochloride;cis-4-Phenylthio-L-proline hydrochloride;

Chemical Property of cis-4-Phenylthio-L-proline hydrochloride

Chemical Property:

• PSA: 74.63000
• LogP: 2.72460
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

(4S)-4-(Phenylthio)-L-prolineHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (4S)-4-(Phenylthio)-L-proline is an impurity of Zofenopril (Z587000).

Technology Process of cis-4-Phenylthio-L-proline hydrochloride

There total 4 articles about cis-4-Phenylthio-L-proline hydrochloride 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:

(2S,4S)-4-(phenylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (83623-88-5) → C11H13NO2S*ClH (105107-84-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 2h;

Reference yield:

N-(benzyloxycarbonyl)-cis-4-(phenylthio)-L-proline (75176-28-2) → (2S,4S)-4-Phenylsulfanyl-pyrrolidine-2-carboxylic acid; hydrobromide (105107-84-4)

Guidance literature:

With hydrogen bromide; In acetic acid; for 1h; Heating;

DOI:10.1021/jm00401a014

Reference yield:

thiophenol (108-98-5) → (2S,4S)-4-Phenylsulfanyl-pyrrolidine-2-carboxylic acid; hydrobromide (105107-84-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Na, 2.) 1N NaOH / 1.) EtOH, 20 h

2: HBr / acetic acid / 1 h / Heating

With sodium hydroxide; hydrogen bromide; sodium; In acetic acid;

DOI:10.1021/jm00401a014

upstream raw materials:

N-(benzyloxycarbonyl)-cis-4-(phenylthio)-L-proline

thiophenol

N-<(phenylmethoxy)carbonyl>-4(R)-<<(4-methylphenyl)sulfonyl>oxy>-(S)-proline methyl ester

(2S,4S)-4-(phenylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Downstream raw materials:

(2S,4S)-4-Phenylsulfanyl-pyrrolidine-2-carboxylic acid methyl ester; hydrochloride

[1(S),4S]-1-[N-(1-Carboxy-3-phenylpropyl)-L-alanyl]-4-(phenylthio)-L-prolin

(2S,4S)-1-[(S)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-4-phenylsulfanyl-pyrrolidine-2-carboxylic acid methyl ester

zofenopril

Refernces

• 1、 Krapcho,Turk,Cushman,Powell,DeForrest,Spitzmiller,Karanewsky,Duggan,Rovnvak,Schwartz,Natarajan,Godfrey,Ryono,Neubeck,Atwa,Petrillo Jr.. "Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines". . p. 1148 - 1160. Retrieved 2007/10/02.