Sodium Hydroxide → 4-Methyl-2-[5-(2-propyl-piperidin-1-yl)-4'-trifluoromethyl-biphenyl-3-yl]-pentanoic acid

HRID 889686Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-methyl-2-[5-(2-propyl-piperidin-1-yl)-4′-trifluoromethyl-biphenyl-3-yl]-pentanoic acid ethyl ester (24 mg, 0.05 mmol) in MeOH (1 mL) was added 3N NaOH (0.200 mL) and heated to 60° 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-(2-propyl-piperidin-1-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-7c018116987a4a129d76b87557480585
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252935B2

Reaction notes

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