(R)-3-(Acetylthio)isobutyryl Chloride

Base Information

• Chemical Name: (R)-3-(Acetylthio)isobutyryl Chloride
• CAS No.: 74345-73-6
• Molecular Formula: C6H9ClO2S
• Molecular Weight: 180.655
• Hs Code.: 2930909090
• European Community (EC) Number: 677-083-0
• DSSTox Substance ID: DTXSID00474040
• Nikkaji Number: J283.176G
• Wikidata: Q72435877
• Mol file: 74345-73-6.mol

Synonyms:74345-73-6;(R)-3-(Acetylthio)isobutyryl Chloride;S-[(2R)-3-chloro-2-methyl-3-oxopropyl] ethanethioate;(2R)-3-Acetylthio-2-methylpropionyl Chloride;(R)-3-(ACETYLTHIO)-2-METHYLPROPIONYLCHLORIDE;SCHEMBL607225;DTXSID00474040;LUDPWTHDXSOXDX-SCSAIBSYSA-N;AKOS025295688;(R)-3-acetylthio-2-methylpropanoyl chloride;(2R)-3-(ACETYLSULFANYL)-2-METHYLPROPANOYL CHLORIDE

Chemical Property of (R)-3-(Acetylthio)isobutyryl Chloride

Chemical Property:

• Vapor Pressure: 0.071mmHg at 25°C
• Refractive Index: 1.491
• Boiling Point: 229.078 °C at 760 mmHg
• Flash Point: 92.344 °C
• PSA: 59.44000
• Density: 1.224 g/cm³
• LogP: 1.66760
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 180.0011784
• Heavy Atom Count: 10
• Complexity: 147

Purity/Quality:

99% ^*data from raw suppliers

(2R)-3-Acetylthio-2-methylpropionylChloride ^*data from reagent suppliers

Safty Information:

• Statements: 34
• Safety Statements: 36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CSC(=O)C)C(=O)Cl
• Isomeric SMILES: C[C@H](CSC(=O)C)C(=O)Cl
• Uses: (2R)-3-Acetylthio-2-methylpropionyl Chloride is a reactant used in the preparation of Captopril (C175750) analogs as inhibitors of angiotensin converting enzyme.

Technology Process of (R)-3-(Acetylthio)isobutyryl Chloride

There total 4 articles about (R)-3-(Acetylthio)isobutyryl Chloride 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: 98.0%

(2S)-3-acetylthio-2-methylpropionic acid (76497-39-7) → (2R,S)-3-Acetylthio-2-methylpropanoyl chloride (74345-73-6)

Guidance literature:

With thionyl chloride; In dichloromethane; at 20 - 40 ℃; for 3h;

Reference yield:

(R)-3-acetylsulfanyl-2-methyl-propionic acid (74431-52-0) → (2R,S)-3-Acetylthio-2-methylpropanoyl chloride (74345-73-6)

Guidance literature:

With pyridine; thionyl chloride; In toluene; for 1.5h; Ambient temperature;

DOI:10.1021/jm00379a013

Reference yield:

3-(acetylthio)-2-methylpropanoic acid (33325-40-5) → (2R,S)-3-Acetylthio-2-methylpropanoyl chloride (74345-73-6)

Guidance literature:

Multi-step reaction with 3 steps

1: acetone / 8 h / 30 °C

2: hydrogenchloride / water; ethyl acetate / 1 h / 30 °C

3: thionyl chloride / dichloromethane / 3 h / 20 - 40 °C

With hydrogenchloride; thionyl chloride; In dichloromethane; water; ethyl acetate; acetone;

upstream raw materials:

(2S)-3-acetylthio-2-methylpropionic acid

(R)-3-acetylsulfanyl-2-methyl-propionic acid

3-(acetylthio)-2-methylpropanoic acid

Downstream raw materials:

(R)-N-<3-(acetylthio)-2-methylpropanoyl>-N-cyclopentylglycine tert-butyl ester

tert-butyl (4S)-3-<(2S)-3-acetylthio-2-methylpropanoyl>-2-oxazolidone-4-carboxylate

tert butyl (4R)-3-<(2S)-3-acetylthio-2-methylpropanoyl>-2-thiazolidone-4-carboxylate

tert-butyl 3-<(2S)-3-acetylthio-2-methylpropanoyl>-1-tetrahydropyranyl-2-imidazolidone-4-carboxylate

Refernces

• 1、 Brem, Jürgen,Van Berkel, Sander S.,Zollman, David,Lee, Sook Y.,Gileadi, Opher,McHugh, Peter J.,Walsh, Timothy R.,McDonough, Michael A.,Schofield, Christopher J.. "Structural basis of metallo-β-lactamase inhibition by captopril stereoisomers". supporting information. p. 142 - 150. Retrieved 2016/02/19.
• 2、 Jang, Doo Ok,Park, Doo Jin,Joonggon, Kim. "A mild and efficient procedure for the preparation of acid chlorides from carboxylic acids". . p. 5323 - 5326. Retrieved 2007/10/03.