Process for preparing (trans)-4-substituted-dl-proline...

Details Process for preparing (trans)-4-substituted-dl-proline... Process for preparing (trans)-4-substituted-dl-proline...

C - Chemistry, Metallurgy

07

D

260/323

C07D 207/16 (2006.01)

Patent

CA 2006615

HA459 Abstract PROCESS FOR PREPARING (TRANS)-4-SUBSTITUTED-PROLINE-DL- DERIVATIVES A process is provided for preparing (trans)-4-phenyl-DL-proline derivatives, which are useful in preparing certain angiotensin converting enzyme inhibitors, which process involves reacting an ester of the structure Image wherein X is a leaving group such as tosylate, R3 is lower alkyl, R is cyclohexyl, phenyl or substituted phenyl, and R1a is a protecting group, with a potassium amide base such as potassium hexamethyldisilazide under reduced temperatures to form the trans-4-substituted proline ester derivative of the structure HA459 Image then hydrolyzing the proline ester to the acid of the structure Image and removing the R1a nitrogen protecting group to form the unprotected acid of the structure Image .

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