Lithium hydroxide, monohydrate → 3-(2-{4-[4-Isopropyl-2-(2-trifluoromethyl-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-vinyl)-benzoic acid

HRID 2261852Notes

Reaction equation

C[O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[N:21]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([F:37])([F:36])[F:35])[N:22]=[CH:23][C:24]=3[CH:25]([CH3:27])[CH3:26])=[CH:14][C:13]=2[CH3:38])[CH:5]=1.[Li+].[OH-].O>O1CCOCC1>[CH:25]([C:24]1[CH:23]=[N:22][N:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:35])([F:36])[F:37])[C:20]=1[CH2:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH:11]=[CH:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:39])=[O:2])=[C:13]([CH3:38])[CH:14]=1)([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-(2-{4-[4-isopropyl-2-(2-trifluoromethyl-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-vinyl)-benzoic acid methyl ester (136 mg, 0.25 mmol) in 1,4-dioxane (7 mL) is added 2N LiOH/H2O (3 mL). The reaction mixture is stirred at 50° C. overnight. The solvent is evaporated and the residue is partitioned between EtOAc and 1N HCl. The layers are separated and the organic phase is washed with water and concentrated to give the title compound (129 mg, 97%). LC-ES-MS m/e 521 (M+1), 100%.

Workup

customThe solvent is evaporated
customthe residue is partitioned between EtOAc and 1N HCl
customThe layers are separated
washthe organic phase is washed with water
concentrationconcentrated

Sources & evidence

ORD record: ord-0745c7947a1740cbb8f04799bc157542
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846960B2

Reaction notes

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