117017-04-6

Basic information

• Product Name: (αR)-Acetyloxybenzenebutanoic Acid
• Synonyms: (αR)-Acetyloxybenzenebutanoic Acid
• CAS NO: 117017-04-6
• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 222.23716
• Product Categories: Aromatics, Chiral Reagents, Intermediates
• Mol File: 117017-04-6.mol

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Ethyl Acetate, Methanol
• CAS DataBase Reference: (αR)-Acetyloxybenzenebutanoic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: (αR)-Acetyloxybenzenebutanoic Acid(117017-04-6)
• EPA Substance Registry System: (αR)-Acetyloxybenzenebutanoic Acid(117017-04-6)

Safety Data

• Hazardous Substances Data: 117017-04-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(αR)-Acetyloxybenzenebutanoic Acid is used as a reactant for the preparation of Benazepril (B119750), which is an angiotensin-converting enzyme (ACE) inhibitor. It is utilized in the treatment of hypertension and heart failure, as well as in the management of certain types of kidney disease. The compound's role in the synthesis of Benazepril highlights its importance in the development of life-saving medications.

Upstream product

• 108-05-4 vinyl acetate 
• 4263-93-8 2-hydroxy-4-phenylbutanoic acid 
• 883723-47-5 2-acetoxy-4-phenylbutanoic acid 
• 188540-85-4 (R)-2-acetoxy-4-oxo-4-phenylbutyric acid 
• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 

Downstream Products

• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 123736-87-8 (S)-2-acetoxy-4-phenylbutanoic acid 
• 115016-95-0 (S)-2-hydroxy-4-phenylbutanoic acid 
• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 

Relevant articles and documents

Enantio-complementary deracemization of (±)-2-hydroxy-4- phenylbutanoic acid and (±)-3-phenyllactic acid using lipase-catalyzed kinetic resolution combined with biocatalytic racemization

Deracemization of (±)-3-phenyllactic acid (1) and (±)-2-hydroxy-4-phenylbutanoic acid (2) was accomplished by lipase-catalysed kinetic resolution coupled to biocatalytic racemization of the non-reacting substrate enantiomers using Lactobacillus paracasei DSM 20008. Cyclic repetition of this sequence led to a single enantiomeric product from the racemate. Access to both enantiomers was achieved by switching between lipase-catalysed acyl-transfer and ester hydrolysis reactions. Both products constitute important building blocks for virus protease- and ACE-inhibitors, respectively.

Process for producing optically active 2-hydroxy-4-arylbutyric acid or its ester

Provided is an industrially useful process for producing an optically active 2-hydroxy-4-arylbutyric acid or its ester. An optically active acyloxysuccinic anhydride is reacted with an aromatic compound in the presence of a Lewis acid to produce an optically active 2-acyloxy-4-oxo-4-arylbutyric acid. The 2-acyloxy-4-oxo-4-arylbutyric acid is converted to an optically active 2-acyloxy-4-arylbutyric acid through catalytic reduction. The 2-acyloxy-4-arylbutyric acid is hydrolyzed in the presence of an acid or an alkali to produce an optically active 2-hydroxy-4-arylbutyric acid. The 2-hydroxy-4-arylbutyric acid is reacted with an alcohol in the presence of an acid to produce an optically active 2-hydroxy-4-arylbutyric acid ester.

Enzymatic resolution of 2-hydroxy-4-phenylbutanoic acid and 2-hydroxy-4-phenylbutenoic acid

Racemic 2-hydroxy-4-phenylbutanoic acid and 2-hydroxy-4-phenyl-butenoic acid have been resolved using a lipase. In each case, the (R)-2-hydroxy and the (S)-2-acetoxy acids were isolated with high enantiomeric excess and yield.

Pyridazodiazepine derivatives

Compounds of the formula STR1 wherein R1 and R2 each independently represent hydrogen, C1 -C10 -alkyl, adamantyl-(C1 -C4 -alkyl) or (C2 -C6 -alkanoyloxy)-(C1/sub