130368-70-6

Upstream product

• 88081-65-6 (2R)-2-(4-toluenesulfonyloxy)propionyl chloride 
• 83056-79-5 (4S)-1-methyl-2-oxoimidazolidine-4-carboxylic acid t-butyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 109579-04-6 methyl (2R)-2-{[(4-methylphenyl)sulfonyl]oxy}propanoate 
• 130368-69-3 (2R)-2-(4-Toluenesulfonyloxy)propionic Acid 
• 100-46-9 benzylamine 

Downstream Products

• 89371-38-0 tert-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate 
• 89371-44-8 (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-carboxy-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid 
• 144069-25-0 (4S)-3-<(2S)-2-propionyl>-1-methyl-2-oxoimidazolidine-4-carboxylic acid 
• 89460-20-8 tert-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate 
• 144069-20-5 tert-butyl (4S)-3-<(2S)-2-propionyl>-1-methyl-2-oxoimidazolidine-4-carboxylate 

Relevant academic research and scientific papers

2-Oxoimidazolidine-4-carboxylate as a novel chiral auxiliary for kinetic resolution

A kinetic resolution by stereospecific amination using 2-oxoimidazolidine-4-carboxylate as a novel chiral auxiliary was investigated. The reaction of tert-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxoimidazolidine-4-carboxylate (5) with an equimolar benz

Studies on angiotensin converting enzyme inhibitors. VI. Synthesis and angiotensin converting enzyme inhibitory activities of the dicarboxylic acid derivative of imidapril and its diastereoisomers

All possible diastereoisomers of the dicarboxylic acid (10a), the biologically active form of imidapril (1), were synthesized, and their inhibitory activity against angiotensin converting enzyme (ACE) was examined. The in vitro ACE inhibitory activity of these compounds greatly depended on the configurations of the three asymmetric carbons in each molecule. The (S,S,S) isomer (10a) showed much more potent activity than the others.

Studies on angiotensin converting enzyme inhibitors. V. The diastereoselective synthesis of 2-oxoimidazolidine derivatives

A diastereoselective synthesis of imidapril (1), which is under clinical study as an antihypertensive drug based on its angiotensin converting enzyme (ACE)-inhibitory activity, was established. N-Alkylation of (2S)-2-amino-4-phenylbutyric acid ester (12) with 3-((2R)-2-methane or toluenesulfonyloxypropionyl)-2-oxoimidazolidine derivative (11) diastereoselectively proceeded in an SN2 fashion to afford tert-butyl (4S)-3-[(2S)-2-[N-[(1S)-1-ethoxycarbonyl)-3-phenylpropyl]amino]propionyl]- 1-methyl-2-oxoimidazolidine-4-carboxylate (13), a precursor of 1. Alternatively, benzyl (2S)-2-[N-(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]propionate (15), which is the key building block of 13, was synthesized by the same strategy. This procedure was also applied to the synthesis of enalapril.

Process for preparing optically active 2-oxoimidazolidine derivatives

Disclosed are a process for preparing an optically active 2-oxoimidazolidine derivative of the formula: STR1 wherein R1 represents hydrogen atom or a lower alkyl group, according to the process described in the specification; and a 3-acyl-2-oxo