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

HRID 333824Notes

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 (Example 135, 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 aqueous HCl (0.3 mL). The precipitate was filtered and dried under high vacuum, leading to the title compound as white solid (54 mg). MS (m/e)=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-dbc95b67ebef4aa2bc1884d2f9066263
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883786B2

Reaction notes

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