[NH2:1][C@H:2]([C:4]([N:6]1[CH2:20][C@@H:19]([S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][C@H:7]1[C:8]([O:10]CC1C=CC=CC=1)=[O:9])=[O:5])[CH3:3].[H][H]>[Pd].C(O)C>[NH2:1][C@H:2]([C:4]([N:6]1[CH2:20][C@@H:19]([S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3]To a solution of 5.0 grams of 1-(L-alanyl)-4-(S)-(phenylthio)-L-proline, phenylmethyl ester in 200 ml. of aqueous ethanol there is added 1 gram of freshly prepared palladium black and the mixture is hydrogenated at 50 psi of hydrogen. The reaction mixture is filtered and concentrated under reduced pressure to yield the desired (S)-1-(L-alanyl)-4-(phenylthio)-L-proline.
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