[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:20](Br)[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22].[OH-].[Na+].O>CN(C)C=O>[CH2:20]([O:11][C:10](=[O:12])[CH:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]A solution of N-tert-butoxycarbonyl-2-(4-hydroxyphenyl) glycine (9.18 g.), phenacyl bromide (6.86 g.) and sodium hydroxide (1.37 g.) in N,N-dimethylformamide (100 ml.) was stirred for 4 hours at ambient temperature. The reaction mixture was poured into water (500 ml.) and extracted three times with every 50 ml. portions of ethyl acetate. The combined extract was washed with water, dried over magnesium sulfate, and evaporated to dryness under reduced pressure to give an oily N-tert-butoxycarbonyl-2-(4-hydroxyphenyl)glycine phenacyl ester (13.19 g.).
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