O=[C:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([NH2:5])=[O:4].[NH2:14][C@H:15]([C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([OH:23])=[O:22])=[O:18])[CH3:16].C([BH3-])#N.[Na+]>>[NH2:5][C:3]([CH:2]([NH:14][C@H:15]([C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([OH:23])=[O:22])=[O:18])[CH3:16])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]In the manner described in example 26, one can condense 2-oxo-4-phenylbutyramide and L-alanyl-L-proline in the presence of sodium cyanoborohydride to yield N-(1-amino carbonyl-3-phenylpropyl)-L-alanyl-L-proline.
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