Potassium Hydroxide → HCID 25268345, compound

HRID 889700Notes

Reaction equation

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

Participants

Conditions

Temperature: 78 °C

Procedure

To a solution of 2-[5-(1-Benzyl-6-trifluoromethyl-piperidin-2-yl)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid ethyl ester, compound 8a (38 mg, 0.062 mmol), in EtOH (3 mL) was added 2M KOH (310 μl, 0.62 mmol). The reaction was heated to 78° C. for 1.5 hours, cooled to room temperature, and concentrated in vacuo. Purification via Gilson HPLC, followed by salt exchange with aqueous 1N HCl gave the product as a light yellow solid. (18.6 mg, 52%) 1H NMR (300 MHz, MeOD) δ ppm 0.81-0.88 (m, 6 H) 1.42 (dd, J=13.38, 6.59 Hz, 1 H) 1.55 (dd, J=13.56, 7.16 Hz, 2 H) 1.63-1.76 (m, 4 H) 1.82-1.97 (m, 2 H) 3.39-3.49 (m, 1 H) 3.61 (td, J=7.82, 2.83 Hz, 1 H) 3.68-3.77 (m, 3 H) 6.96-7.09 (m, 5 H) 7.29-7.37 (m, 2 H) 7.43 (s, 1 H) 7.58-7.66 (m, 4 H) Calcd for C32H33F6NO2 (M+H) 577.60, Found 578.4.

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
customPurification via Gilson HPLC

Sources & evidence

ORD record: ord-cf1de228e8b3410ca692b9f26380d355
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252935B2

Reaction notes

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