109010-59-5

Upstream product

• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 88330-79-4 ethyl-(Z)-2-hydroxy-4-oxo-4-phenyl-but-2-enoate 
• 159974-68-2 (R)-3,4-dihydroxy-1-phenylbutan-1-one 
• 156386-82-2 trans-γ-3-benzoylprop-2-en-1-ol 
• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 146912-66-5 (R)-2-hydroxy-4-oxo-4-phenylbutanoic acid 
• 1005327-17-2 (R)-1-phenyl-2-(2-phenyl-1,3,2-dioxaborolan-4-yl)ethanone 
• 244277-48-3 ethyl (R)-(-)-2-hydroxy-4-oxo-4-phenylbutanoate 

Downstream Products

• 133608-98-7 (R)-2-tert-Butoxycarbonyl-3-phenethyl-succinic acid 1-tert-butyl ester 4-ethyl ester 
• 86541-77-7 (3S)-1-(carboxymethyl)-<<(1S)-1-(ethoxycarbonyl)-3-phenylpropyl>amino>-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one hydrochloride 
• 109010-61-9 (2S,3'S)-2-(1-tert-butoxycarbonylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester 
• 106860-19-9 (1S,9S)-t-butyl 9-<(1S)-ethoxycarbonyl-3-phenylpropylamino>octahydro-10-oxo-6H-pyridazino<1,2-a><1,2>diazepine-1-carboxylate 
• 133609-00-4 (R)-2-Phenethyl-succinic acid 1-ethyl ester 
• 110221-37-9 (S)-2-((2S,6R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester 
• 113955-29-6 (S)-2-((R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid ethyl ester 
• 111902-57-9 temocapril 
• 113955-30-9 (S)-2-((R)-4-Carboxymethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid ethyl ester 
• 113955-31-0 (S)-2-((R)-4-Carboxymethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid 

Relevant academic research and scientific papers

Chloramphenicol base chemistry. Part 10: Asymmetric synthesis of α-hydroxy chiral alcohols via intramolecular Michael additions of γ-hydroxy-α, β-unsaturated enones with chloramphenicol base derived bifunctional urea organocatalysts

We have developed the chloramphenicol base urea-catalyzed intramolecular Michael addition of γ-hydroxy-α, β-unsaturated enones. The oxidation of the resulting products provided facile access to the corresponding α-hydroxy chiral alcohols with good efficiency and enantioselectivity, with the reaction displaying broad substrate scope. The utility of this methodology was further demonstrated by the synthesis of (R)-2-hydroxy-4-phenylbutanoate, which is a key building block for the construction of the ACE inhibitor benazepril hydrochloride.

An improved method for preparing of the benazepril hydrochloride and containing the pharmaceutical composition of the benazepril hydrochloride

The invention discloses an improved preparation method of benazepril hydrochloride and pharmaceutical composition containing the benazepril hydrochloride. With the adoption of the preparation method, the safety is high, the cost is low, the clean production value is high, industrial production is easy to realize, and meanwhile, the pharmaceutical composition is easy to prepare and use.

Ethyl 2,4-dioxo-4-phenylbutyrate: A versatile intermediate for the large-scale preparation of enantiomerically pure α-hydroxy and α-amino acid esters

Starting from ethyl 2,4-dioxo-4-phenylbutyrate, both enantiomers of six enantiomerically pure α-hydroxy and α-amino acid esters (homophenylalanine derivatives) were prepared on >100 g scale. The key step involves a Pt-cinchona catalyzed enantioselective hydrogenation followed by enrichment via crystallization. All derivatives are commercially available.

An efficient synthesis of optically active 2-alkylsuccinate monoesters

Optically active 2-alkylsuccinates were obtained as their monoesters by stereospecific substitution of the p-toluenesulfonates or p-nitrobenzenesulfonates of α-hydroxy esters with sodium di-tert-butyl malonate, followed by hydrolysis and decarboxylation of the resulting diacids.