Sodium Hydroxide → 4-Methyl-2-(5-piperidin-4-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid

HRID 889749Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of a mixture of 4-methyl-2-(5-piperidin-4-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester and methyl ester (43 mg, 0.10 mmol) in MeOH (1 mL) was added 3N NaOH (0.10 mL) and heated to 50° C. for 2 h. The reaction was concentrated in vacuo to remove MeOH. The thick liquid was acidified to pH=2 by 2N HCl. The resulting acidic solution was extracted with EtOAc. The organic fraction was dried (MgSO4) and concentrated in vacuo. The crude mixture was purified by Gilson reverse phase column chromatography to obtain 4-methyl-2-(5-piperidin-4-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid.

Workup

concentrationThe reaction was concentrated in vacuo
customto remove MeOH
extractionThe resulting acidic solution was extracted with EtOAc
dry with materialThe organic fraction was dried (MgSO4)
concentrationconcentrated in vacuo
customThe crude mixture was purified by Gilson reverse phase column chromatography

Sources & evidence

ORD record: ord-b4d6ac66d325464c835499f18fff3cd8
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252935B2

Reaction notes

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