76497-39-7

Basic information

• Product Name: D-(-)-3-Acetylthio-2-methylpropionic acid
• Synonyms: D(-)S-ACETYL-BETA-MERCAPTO ISOBUTYRIC ACID;D-(S)-3-ACETYL-3-MERCAPTO-2-METHYL PROPANOIC ACID;D-(-)-3-ACETYLSULFANYL-2-METHYLPROPIONIC ACID;d-(-)-3-acetylthio-2-methylpropionic acid;(S)-BETA-(ACETYLMERCAPTO)ISOBUTYRIC ACID;(S)-(-)-BETA-ACETYLTHIO-2-METHYLPROPIONIC ACID;(S)-(-)-3-(ACETYLMERCAPTO)ISOBUTYRIC ACID;(S)-(-)-3-ACETYLTHIO-2-METHYLPROPANOIC ACID
• CAS NO: 76497-39-7
• Molecular Formula: C₆H₁₀O₃S
• Molecular Weight: 162.21
• EINECS: 278-480-8
• Product Categories: Carboxylic Acids (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry
• Mol File: 76497-39-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 5 °C
• Boiling Point: 120-132 °C (1 mmHg)
• Flash Point: >230 °F
• Appearance: /liquid
• Density: 1.178 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0013mmHg at 25°C
• Refractive Index: n20/D 1.490
• Storage Temp.: Store at 0-5°C
• PKA: 4.22±0.10(Predicted)
• Water Solubility: INSOLUBLE
• CAS DataBase Reference: D-(-)-3-Acetylthio-2-methylpropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: D-(-)-3-Acetylthio-2-methylpropionic acid(76497-39-7)
• EPA Substance Registry System: D-(-)-3-Acetylthio-2-methylpropionic acid(76497-39-7)

Safety Data

• Hazard Codes: C,T
• Statements: 34-36-24/25
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 76497-39-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to slightly yellow liquid

Uses

Different sources of media describe the Uses of 76497-39-7 differently. You can refer to the following data:
1. S-Acetylthio-2-methylpropionic acid (S-AMPA) is a key chiral intermediate for Captopril (C175750) and other hypertension drugs.
2. ACE-inhibitors.

InChI:InChI=1/C6H10O3S/c1-4(6(8)9)3-10-5(2)7/h4H,3H2,1-2H3,(H,8,9)/p-1/t4-/m1/s1

Upstream product

• 97101-46-7 methyl L-(+)-3-acetylthio-2-methylpropionate 
• 33325-40-5 3-(acetylthio)-2-methylpropanoic acid 
• 26473-47-2 2-methyl-3-sulfanylpropanoic acid 
• 108-24-7 acetic anhydride 
• 75172-11-1 (S)-3-mercapto-2-methyl-propionic acid 

Downstream Products

• 64805-62-5 (S)-1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-proline 

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.

Development of odorless organosulfur reagents and asymmetric reaction using odorless thiols

Odorless organosulfur reagents were developed by increasing their molecufar weights to suppress vohtility. 1-Dodecanethiol (4), dodecyl methyl sulfide (5), p-heptylphenylmethanethiol (6), p-dodecylbenzenethiol (7), p-heptylbenzenethiol (8), 2-dodecyl-l,3-propanedithiol (11), p-octyloxyphenylmethanethiol (18b,), and p-octyloxybenzenethiol (19) are typical examples of the odorless thiols and sulfides. 6-Morpholinohexyl thiol (15), methyl 6-morpholinohexyl sulfide (16) and methyl 6-morpholinohexyl sulfoxide (17,) were also developed as separable reagents from reaction products by facile acid-base extraction. In addition, p-tetramethylsilylphenylmethanethiol (18) and p-tetramethylsilylbenzenethiol (14) were synthesized as the odorless synthetic substitutes of benzyl mercaptan and benzenethiol, respectively. In a similar way, silylated diphenyl disulfide (26) and diselenide (21) were prepared as odorless disulfide and diselenide. Moreover, 10-sulfanylisobomeol (1) was found to be an excellent chiral odorless substitute of hydrogen sulfide in Michael addition.

Effect of the α-methyl substituent on chemoselectivity in esterase-catalyzed hydrolysis of S-acetyl sulfanylalkanoates

(Equation Presented) The isomeric compounds 1 and 3, which differ only in the position of a methyl substituent, give opposite chemoselectivities in an esterase-catalyzed hydrolysis reaction. The esterase was chemoselective for the oxoester in 1, but for the thiol ester group in 3. A high enantioselectivity was observed for both 1 and 3.