D-(-)-3-Acetylthio-2-methylpropionic acid, CAS No. 76497-39-7

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76497-39-7

Catalog No. EBD51960

CAS 76497-39-7

Name D-(-)-3-Acetylthio-2-methylpropionic acid

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Basic Information

Synonyms: D-(-)-S-Acetyl-beta-mercaptoisobutyricacid D-(-)-3-Acetylthio-2-methylpropionicacid (-)-3-(Acetylthio)-2-methylpropanoicacid D-3-(Acetylthio)-2-methylpropanoicacid 3-(acetylthio)-2-methylpropionicacid 3-(acetylsulfanyl)-2-methylpropanoicacid (2S)-3-(acetylsulfanyl)-2-methylpropanoicacid (2S)-3-(acetylsulfanyl)-2-methylpropanoate D-3-acetylthio-2-methylpropionicacid

Molecular Formula: C6H10O3S

Molecular Weight: 162.21

MDL Number: MFCD00066543

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates Medicinal Chemistry > Biochemicals and Life Science Reagents > Amino Acids and Derivatives

Product Description:

(S)-3-Acetylthio-2-methylpropanoic acid is a chiral sulfur-containing carboxylic acid derivative. It serves as a key chiral building block in the synthesis of captopril, a widely used angiotensin-converting enzyme (ACE) inhibitor for the treatment of hypertension and heart failure. The (S)-configuration at the 2-methyl position is crucial for the biological activity of the final drug molecule. This compound is specifically utilized as an advanced intermediate in the production of captopril and its analogs. Its structure incorporates both a protected thiol group (as the acetyl thioester) and a carboxylic acid functionality, allowing for selective deprotection and further coupling reactions to construct the final active pharmaceutical ingredient (API).

Physical Properties

Melting Point: 5 °C

Boiling Point: 120-132 °C (1 mmHg)

Flash Point: >230 °F

Density: 1.178 g/mL at 20 °C(lit.)

Solubility: INSOLUBLE

Refractivity: n20/D 1.490

Storage: Store at 0-5°C

Analytical Data

Appearance: clear colourless to slightly yellow liquid