HCID 131714797, compound → HCID 13657310, compound

Participants

Reaction Steps

A mixture of 1-[[[(3S)-3-(benzoylamino)-2-hydroxy-4-phenylbutyl]methylamino]carbonyl]-L-proline, phenylmethyl ester (isomer A) (790 mg., 149 mmole), palladium hydroxide on carbon catalyst (110 mg.) and ethanol: ethyl acetate (1:1, 20 ml.) is stirred under hydrogen gas (balloon) for one hour. The solution is filtered (millipore), and the solvent removed at reduced pressure to give the desired product as a colorless solid. Drying under vacuum over phosphorus pentoxide yields 569 mg. of 1-[[[(3S)-3-(benzoylamino)-2-hydroxy-4-phenylbutyl]methylamino]carbonyl]-L-proline (isomer A); m.p. 108°-117°; [α]D20 =-77.5° (c=1.4, methanol). TLC (silica gel; chloroform:methanol:acetic acid; 18:1:1) Rf =0.39, trace at Rf =0.58.

Provenance & Evidence