[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][C@H:12]([C:24]([OH:26])=[O:25])[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])([O-])=O.CO.[Cl-].[NH4+]>[Zn]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][C@H:12]([C:24]([OH:26])=[O:25])[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15]To a yellow solution of 17.0 g (45.2 mmol) of S-(o-nitrophenyl)-N-carbobenzyloxy-D-cysteine in 800 mL of methanol containing 4.84 g (90.4 mmol) of ammonium chloride (NH4Cl) was added 41.1 g (633 mmol) of zinc dust. The resulting gray slurry was refluxed for 4 hours. The hot solution was then filtered, and the solid residue washed with an additional 200 mL of methanol. The filtrate was evaporated and the solid residue triturated with 320 mL of 1N HCl. Upon stirring for 1/2 hour, the initial gummy mass crystallized to a white solid. Filtration of the solid yielded 13.1 g (84%) of S-(o-aminophenyl)-N-carbobenzyloxy-D-cysteine.
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