Potassium Hydroxide → 4-Methyl-2-{4'-trifluoromethyl-5-[1-(4-trifluoromethyl-benzoyl)-piperidin-3-yl]-biphenyl-3-yl}-pentanoic acid

HRID 889722Notes

Reaction equation

C([O:3][C:4](=[O:44])[CH:5]([C:10]1[CH:11]=[C:12]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22](=[O:33])[C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[OH-].[K+]>CCO>[CH3:8][CH:7]([CH3:9])[CH2:6][CH:5]([C:10]1[CH:11]=[C:12]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:41])[F:42])=[CH:36][CH:35]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22](=[O:33])[C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][CH:24]=3)[CH2:17]2)[CH:15]=1)[C:4]([OH:44])=[O:3]

Participants

Conditions

Temperature: 78 °C

Procedure

To a solution of compound 43a, 4-Methyl-2-{4′-trifluoromethyl-5-[1-(4-trifluoromethyl-benzoyl)-piperidin-3-yl]-biphenyl-3-yl}-pentanoic acid ethyl ester 60.0 mg, 0.097 mmol) in EtOH (4.8 ml) was added 2M KOH (0.48 ml, 0.48 mmol). The reaction was heated to 78° C. for 1.5 hours, cooled to room temperature, and concentrated in vacuo. Purification via Gilson HPLC, gave the product as a white lyophilate, (21.7 mg, 38%). 1H NMR (300 MHz, MeOD) δ ppm 0.88-0.96 (m, 6 H) 1.42-2.15 (m, 6 H) 2.70-3.24 (m, 3 H) 3.66-3.80 (m, 3 H) 4.68-7.71 (m, 1 H) 7.17 (s, 1 H) 7.32-7.81 (m, 10 H), Calcd for C32H31F6NO3 (M+H) 591.58, Found 592.3.

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
customPurification via Gilson HPLC
customgave the product as a white lyophilate, (21.7 mg, 38%)

Sources & evidence

ORD record: ord-815ed61388e54fa39fb0f371330335d6
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252935B2

Reaction notes

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