[CH2:1]([O:8][C:9]([N:11]([CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=1)[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].Cl>CO>[CH2:1]([O:8][C:9]([N:11]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:22][CH:23]=1)[CH3:12])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1The methyl 4-(((benzyloxycarbonyl)(methyl)amino)methyl)benzoate was dissolved in methanol, then LiOH (0.35 g, 14.7 mmol) was added. The resulting mixture was maintained at room temperature for 2 days. The mixture was adjusted to pH=1˜2 with 2N aqueous hydrochloric acid then extracted with ethyl acetate (50 mL×3). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and condensed under vacuum. The residue was purified by silica gel chromatography (petrol ether:ethyl acetate=10:1) to yield a white solid of 4-(((benzyloxycarbonyl)(methyl)amino)methyl)benzoic acid (1.25 g, 56.8%), LC-MS (ESI) m/z 300 [M+1]+.
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