Lithium hydroxide, monohydrate → [2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid

HRID 1161315Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To the solution of 24 g (0.055 mol) [2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid ethyl ester in 240 ml dioxan, 240 ml water and 7.0 g (0.166 mol) lithium hydroxide monohydrate were added. The solution was stirred for 2 h at 100° C. After cooling to room temperature the organic solvent was evaporated. Under stirring 162 ml 1M hydrochloric acid were added. The resulting suspension was filtered, the filter cake washed with water and dried under high vacuum to give 21.7 g (95%) of the desired compound as a white solid. MS (ES−): 403 (M−H).

Workup

temperatureAfter cooling to room temperature the organic solvent
customwas evaporated
stirringUnder stirring 162 ml 1M hydrochloric acid
additionwere added
filtrationThe resulting suspension was filtered
washthe filter cake washed with water
customdried under high vacuum

Sources & evidence

ORD record: ord-5b3cdfdd6c234fa08b8dfab8f6885037
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816540B2

Reaction notes

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