Lithium Hydroxide → 3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzoic acid

HRID 1095881Notes

Reaction equation

C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:24])[C:11]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([Cl:23])[CH:18]=2)([OH:16])[C:12]([F:15])([F:14])[F:13])=[C:6]([Cl:25])[CH:5]=1.[Li+].[OH-]>C1COCC1.CO>[Cl:25][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[CH:10]([CH3:24])[C:11]([C:17]1[CH:22]=[CH:21][N:20]=[C:19]([Cl:23])[CH:18]=1)([OH:16])[C:12]([F:15])([F:14])[F:13])[C:3]([OH:26])=[O:2]

Participants

Conditions

Temperature: 65 °C

Procedure

3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzoic acid methyl ester (62 mg) in THF (1.5 mL) and MeOH (0.3 ml) was treated with 1M aqueous LiOH (0.228 ml) and stirred for 2 h at 65° C. (bath-temperature). The organic solvents were evaporated in vacuo and the residue was diluted with water (2 ml) and acidified with 1M-HCl (0.3 ml). The precipitate was filtered and dried under high vacuum, leading to the title compound as a white solid (54 mg). MS (m/e, ISP neg. ion)=392.2 (M−H+).

Workup

customThe organic solvents were evaporated in vacuo
additionthe residue was diluted with water (2 ml)
filtrationThe precipitate was filtered
customdried under high vacuum

Sources & evidence

ORD record: ord-04f5fae761b3460a8b5b31b4b70804e7
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138189B2

Reaction notes

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