Acetic Acid → HCID 67670838, compound

Reaction equation

[CH3:1][O:2][C:3]([C@H:5]1[CH2:30][CH2:29][C@:7]2([O:11][CH2:10][C:9]([C:12]3[CH:17]=[C:16]([N:18]4[CH:22]=[CH:21][N:20]=[C:19]4[C:23]([F:26])([F:25])[F:24])[CH:15]=[CH:14][C:13]=3[O:27][CH3:28])=[CH:8]2)[C@@H:6]1[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)=[O:4].C(O)(=O)C>[OH-].[Pd+2].[OH-].CO>[CH3:1][O:2][C:3]([C@H:5]1[CH2:30][CH2:29][C@:7]2([O:11][CH:10]=[C:9]([C:12]3[CH:17]=[C:16]([N:18]4[CH:22]=[CH:21][N:20]=[C:19]4[C:23]([F:24])([F:25])[F:26])[CH:15]=[CH:14][C:13]=3[O:27][CH3:28])[CH2:8]2)[C@@H:6]1[C:31]1[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=1)=[O:4]

Participants

Procedure

A mixture of 67 mg (0.13 mmol) of (5R,6S,7S)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-(trifluoromethyl)imidazol-1-yl)phenyl)-1-oxaspiro[4.4]non-3-ene-7-carboxylic acid methyl ester (from Example 69), 20% palladium(II) hydroxide on carbon (32 mg), acetic acid (1.2 mL), and methanol (6.0 mL) was stirred at RT under hydrogen at atmospheric pressure. After 20 min., the catalyst was removed using a 0.45 micron filter and washed with additional methanol. The filtrate was concentrated and the residue was purified by preparative TLC, eluting five times in 3% ethyl ether in dichloromethane. This yielded 15 mg of the title compound and 30 mg of (3S,5R,6S,7S)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-(trifluoromethyl)imidazol-1-yl)phenyl)-1-oxaspiro[4.4]nonane-7-carboxylic acid methyl ester.