C[O:2][C:3]([C:5]1([CH:11]=[N:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[OH-].[Na+].Cl>C1COCC1.CO.O>[CH2:14]([O:13][N:12]=[CH:11][C:5]1([C:3]([OH:4])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1A mixture of 1-(benzyloxyimino-methyl)-cyclohexanecarboxylic acid methyl ester (1.75 g, 6.36 mmol) and sodium hydroxide (0.76 g, 19.1 mmol) in THF (10 mL), methanol (10 mL) and water (5 mL) was stirred at room temperature for 40 h. The reaction mixture was acidified to pH 4 with 3N aqueous HCl and was extracted with EtOAc (50 mL×2). The combined organic layers were dried (MgSO4) and were evaporated in vacuo to yield the title compound as a yellow oil. (1.59 g, 96%). MH+262.
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