F. Yun
2004
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Journal
Fine chemicals
Abstract
The technology of synthesis of 2-oxo-4-phenylbutyric acid(OPBA) from benzaldehyde as prochiral intermediate for preparation of angiotensin converting enzyme inhibitor(ACEI) medicines was studied.Cinnamic acid was firstly prepared by condensation of benzaldehyde with acetic anhydride catalyzed by anhydrous potassium acetate,and then hydrogenated with molecular hydrogen and esterified with ethanol to form ethyl 3-phenylpropionate.Condensation of ethyl 3-phenylpropionate with diethyl oxalate gave diethyl 3-benzyl-2-oxosuccinate,which,by hydrolysis with w(H_2SO_4)=15% aqueous sulfuric acid produced the prochiral intermediate OPBA.The key steps of condensation and hydrolysis were optimized.Thus,with ethyl 3-phenylpropionate and diethyl oxalate in molar ratio 1∶3,duration of condensation 1.5 h at 60 ℃,and time of hydrolysis 15 h,yield of OPBA was 65%.