74345-73-6

Basic information

• Product Name: (R)-3-(ACETYLTHIO)-2-METHYLPROPIONYL CHLORIDE
• Synonyms: (R)-S-[2-(CHLOROFORMYL)PROPYL] THIOACETATE;(R)-3-(ACETYLTHIO)-2-METHYLPROPIONYL CHLORIDE;(R)-3-(ACETYLTHIO)ISOBUTYRYL CHLORIDE;(R)-ACETYLTHIO 2-METHYLPROPANOYL CHLORIDE;THIOACETIC ACID (R)-S-[2-(CHLOROFORMYL)PROPYL] ESTER;(R)-3-(ACETHYLTHIO)ISOBUTYRYL CHLORIDE;D-(-)-3-ACETYLTHIO-2-METHYLPROPIONYL CHLORIDE;(2R)-3-Acetylthio-2-methylpropionyl chloride
• CAS NO: 74345-73-6
• Molecular Formula: C₆H₉ClO₂S
• Molecular Weight: 180.65
• Mol File: 74345-73-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 229℃
• Flash Point: 92℃
• Appearance: /
• Density: 1.224
• Vapor Pressure: 0.071mmHg at 25°C
• Refractive Index: 1.491
• CAS DataBase Reference: (R)-3-(ACETYLTHIO)-2-METHYLPROPIONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(ACETYLTHIO)-2-METHYLPROPIONYL CHLORIDE(74345-73-6)
• EPA Substance Registry System: (R)-3-(ACETYLTHIO)-2-METHYLPROPIONYL CHLORIDE(74345-73-6)

Safety Data

• Statements: 34
• Safety Statements: 36/37/39
• Hazardous Substances Data: 74345-73-6(Hazardous Substances Data)

Usage

Description

(R)-3-(ACETYLTHIO)-2-METHYLPROPIONYL CHLORIDE, also known as (2R)-3-Acetylthio-2-methylpropionyl Chloride, is an organic compound that serves as a key reactant in the synthesis of pharmaceuticals. It is characterized by its unique chemical structure, which includes an acetylthio group, a methyl group, and a propionyl chloride moiety. (R)-3-(ACETYLTHIO)-2-METHYLPROPIONYL CHLORIDE plays a crucial role in the development of certain drug analogs, particularly those targeting the inhibition of angiotensin-converting enzyme (ACE).
Used in Pharmaceutical Industry:
(R)-3-(ACETYLTHIO)-2-METHYLPROPIONYL CHLORIDE is used as a reactant for the preparation of Captopril analogs, which are inhibitors of angiotensin-converting enzyme (ACE). These analogs are essential in the development of medications for treating hypertension and congestive heart failure, as they help regulate blood pressure and improve cardiovascular function.
The application of (R)-3-(ACETYLTHIO)-2-METHYLPROPIONYL CHLORIDE in the pharmaceutical industry is primarily due to its ability to contribute to the synthesis of Captopril analogs. These analogs have the potential to offer improved therapeutic effects and reduced side effects compared to existing ACE inhibitors, making them valuable candidates for the development of new medications to address cardiovascular diseases.

InChI:InChI=1/C6H9ClO2S/c1-4(6(7)9)3-10-5(2)8/h4H,3H2,1-2H3/t4-/m1/s1

Upstream product

• 33325-40-5 3-(acetylthio)-2-methylpropanoic acid 
• 74431-52-0 (R)-3-acetylsulfanyl-2-methyl-propionic acid 
• 76497-39-7 (2S)-3-acetylthio-2-methylpropionic acid 

Downstream Products

• 62571-86-2 captopril 
• 188636-22-8 (2R)-1-((2S)-3-(acetylthio)-2-methylpropanoyl)pyrrolidine-2-carboxylic acid 
• 64838-55-7 (2S)-1-[(2S)-3-acetylthio-2-methylpropanoyl]pyrrolidine-2-carboxylic acid 
• 133272-76-1 N-(3-(Acetylthio)-2(S)-methyl-1-oxopropyl)-L-glutamic acid 5-methyl ester 
• 133272-79-4 (2S-cis)-3-(3-(Acetylthio)-2(S)-methyl-1-oxopropyl)-2,4-thiazolidinedicarboxylic acid 4-methyl ester 
• 76783-28-3 (R)-1-((S)-3-Acetylsulfanyl-2-methyl-propionyl)-5-oxo-pyrrolidine-2-carboxylic acid 
• 77999-43-0 (S)-3-((S)-3-Acetylsulfanyl-2-methyl-propionyl)-2-oxo-thiazolidine-4-carboxylic acid 
• 77999-42-9 (S)-3-((S)-3-Acetylsulfanyl-2-methyl-propionyl)-2-oxo-oxazolidine-4-carboxylic acid 
• 77999-45-2 3-((S)-3-Acetylsulfanyl-2-methyl-propionyl)-2-oxo-imidazolidine-4-carboxylic acid 
• 76783-30-7 (2S)-1-<(2S)-3-acetylthio-2-methylpropanoyl>pyroglutamic acid 
• 851512-46-4 (2R,5R)-1-((2'S)-3'-acetylthio-2'-methylpropanoyl)-2,5-bis(methoxymethyl)pyrrolidine 
• 97716-22-8 (2S,2'S)-1-<3-(Acetylthio)-2-methylpropionyl>prolin-methylester 
• 74258-86-9 alacepril 
• 114029-44-6 (2S,4S)-1-((S)-3-Acetylsulfanyl-2-methyl-propionyl)-4-hydroxy-pyrrolidine-2-carboxylic acid 

Relevant articles and documents

Preparing method of captopril isomer

The invention provides a preparing method of a captopril isomer. The method includes the steps of resolving mixed 3-sulfanyl-2-methyl propionic acid into L-3-sulfanyl-2-methyl propionic acid, making L-3-sulfanyl-2-methyl propionic acid react with thionyl chloride to prepare L-3-sulfanyl-2-methylpropionyl chloride (L-acyl chloride for short), making L-acyl chloride react with L-proline or D-prolineto generate 1-(3-sulfanyl-2-methylpropionyl)-proline (free acid for short), and conducting hydrolysis deprotection on the free acid to prepare the isomer. The preparing method is good in resolving effect, the obtained isomer is high in optical purity, the resolving reaction time and temperature range is large, and control is easy.

Asymmetric induction in the conjugate addition of thioacetic acid to methacrylamides with chiral auxiliaries

The conjugate addition of thioacetic acid to methacrylamides with chiral C2-symmetric trans-2,5-disubstituted pyrrolidines afforded the addition products in excellent stereoselectivities (>99% de) and good yields (80-90%). The high selectivity was attributed mainly to the steric effect of the chiral auxiliaries. The cyclic nature of the chiral auxiliaries seemed also important for both the stereoselectivity and the reaction rate. Acidic hydrolysis of the adduct containing (2R,5R)-bis(methoxymethyl)pyrrolidine gave (S)-3-mercapto-2-methylpropanoic acid, a key intermediate for captopril, in 98% ee and 96% yield. The chiral auxiliary was recovered in the demethylated form of N-Boc-(2R,3R)-bis(hydroxymethyl)pyrrolidine in 90% yield.

Thiazaspirane derivatives, process for their preparation, and medicaments

Novel thiazaspirane derivatives of the general formula STR1 including salts thereof with physiologically acceptable acids and bases, processes for their preparation and medicaments containing them.