Acetic Acid → HCID 178445779, compound
Reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[C:13]([C:31]([F:34])([F:33])[F:32])=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH:22]([N+:28]([O-])=O)[CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>[Zn]>[NH2:28][CH:22]([C:17]1[CH:16]=[CH:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([O:11][C@H:8]3[CH2:9][CH2:10][C@H:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]3)[C:13]=2[C:31]([F:33])([F:34])[F:32])[CH:18]=1)[CH2:23][CH2:24][C:25]([OH:27])=[O:26]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Zinc (0.194 g, 2.96 mmol) was added to a solution of 4-[6-(trans-4-tert-butyl-cyclohexyloxy)-5-trifluoromethyl-naphthalen-2-yl]-4-nitro-butyric acid (0.102 g, 0.212 mmol) in acetic acid (3.00 mL, 52.8 mmol). The mixture was stirred for 2 hours at room temperature. HPLC analysis showed that the reaction was complete. The mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. The resulting crude product was dissolved in DMSO (4 mL) and purified by HPLC. The product was dried for 2 days under vacuum to give 28 mg of the title compound as a white solid (26% yield). MS: m/z=435.66 [M-16]+. 1H NMR (MeOD, 400 MHz): δ=8.24-8.30 (m, 1 H), 8.09-8.14 (m, 1 H), 7.92-7.96 (m, 1 H), 7.56-7.65 (m, 2 H), 4.45-4.57 (m, 2 H), 2.65-2.69 (m, 2 H), 2.26-2.46 (m, 4 H), 2.18-2.26 (m, 2 H), 1.87-1.97 (m, 2 H), 1.45-1.58 (m, 2 H), 1.18-1.31 (m, 2 H), 1.06-1.17 (m, 1 H), 0.92 (s, 9 H)