[C:1]([O:5][C:6]([CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:20]([C:21]([O:23]CC)=[O:22])=[CH:19][N:18]=[C:17]([Cl:26])[N:16]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1>[C:1]([O:5][C:6]([CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:20]([C:21]([OH:23])=[O:22])=[CH:19][N:18]=[C:17]([Cl:26])[N:16]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]To a solution of ethyl 4-(4-((tert-butoxycarbonyl)methyl)piperidin-1-yl)-2-chloropyrimidine-5-carboxylate (368 mg, 0.923 mmol) in THF (5 mL), aq. 1M LiOH (2.20 mL, 2.20 mmol) was added. It was heated to reflux for 5 h. THF was removed in vacuo. After being acidified with HOAc (2 mL), the residue was purified by HPLC to give 4-(4-((tert-butoxycarbonyl)methyl)piperidin-1-yl)-2-chloropyrimidine-5-carboxylic acid (150 mg). MS 371.4 and 373.4 (M+H, Cl pattern).
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