Methanol → 1-{4-Methoxy-3-[2-(3-oxetan-3-yl-phenyl)-ethoxy]-benzoylamino}-4-trifluoromethyl-cyclohexanecarboxylic Acid

HRID 1918386Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

77 mg of 1-{4-Methoxy-3-[2-(3-oxetan-3-yl-phenyl)-ethoxy]-benzoylamino}-4-trifluoromethyl-cyclohexanecarboxylic acid methyl ester were dissolved using 3.5 ml of methanol and 173 μl of a 1M aqueous solution of NaOH added. The mixture was stirred at 60° C. for 8 h. The mixture was then poured into 10 ml of water and acidified to pH=5 using 5% aqueous NaHSO4-solution. The mixture was then extracted three times using 15 ml of EA each. The organic layer was then dried using MgSO4 and evaporated.

Workup

additionadded
extractionThe mixture was then extracted three times
customThe organic layer was then dried
customevaporated

Sources & evidence

ORD record: ord-f4b6fca3207f4d5581dc4e632fc608f1
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618304B2

Reaction notes

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