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

HRID 1475798Notes

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-d4cbc7dc2d7c44c8be6814af81d6076c
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018383B2

Reaction notes

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