N-Carbobenzyloxy-4-hydroxy-4-[(4-pyridyl)methyl]-L-prolin → 4-hydroxy-4-[(4-pyridyl)methyl]-L-proline
Reaction equation
C([N:11]1[CH2:18][C:17]([OH:26])([CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O.C(SCC(N1CC=C[C@@]1(CC1OC=CC=1)C(O)=O)=O)(=O)C>>[OH:26][C:17]1([CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH2:18][NH:11][C@H:12]([C:13]([OH:15])=[O:14])[CH2:16]1Participants
3
Procedure
The N-carbobenzyloxy-4-hydroxy-4-[(4-pyridyl)-methyl]-L -proline from part (a) is hydrogenated according to the procedure of Example 1 (b) to yield 4-hydroxy-4-[(4-pyridyl)methyl]-L-proline. This amino acid is reacted with D-3-acetylthio-2-methylpropionyl chloride according to the procedure of Example 1 (c) to yield [1(S)]-1-[3-(acetylthio)-2-methyl-1-oxopropyl]-4-hydroxy-4-[(4-pyridyl)methyl]-L-proline.