Potassium Hydroxide → HCID 25268344, compound

HRID 889698Notes

Reaction equation

C([O:3][C:4](=[O:47])[CH:5]([C:10]1[CH:11]=[C:12]([C:37]2[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=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][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=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:37]2[CH:38]=[CH:39][C:40]([C:43]([F:46])([F:44])[F:45])=[CH:41][CH:42]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH:18]([C:22]([F:23])([F:24])[F:25])[N:17]2[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][CH:28]=2)[CH:15]=1)[C:4]([OH:47])=[O:3]

Participants

Conditions

Temperature: 78 °C

Procedure

To a solution of 4-methyl-2-{4′-trifluoromethyl-5-[6-trifluoromethyl-1-(4-trifluoromethyl-benzyl)-piperidin-2-yl]-biphenyl-3-yl}-pentanoic acid ethyl ester, compound 8a (25 mg, 0.037 mmol), in EtOH (2 mL) was added 2M KOH (74 μl, 0.148 mmol). The reaction was heated to 78° C. for 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 white solid. (2.1 mg, 9%) 1H NMR (300 MHz, MeOD) δ ppm 0.86-0.96 (m, 6 H) 1.43-1.50 (m, 1 H) 1.54-1.64 (m, J=13.52, 6.97, 6.83, 3.58 Hz, 2 H) 1.83-1.98 (m, 5 H) 2.10-2.30 (m, 1 H) 3.58-3.73 (m, 2 H) 3.98 (d, J=17.71 Hz, 3 H) 7.18-7.26 (m, 2 H) 7.35 (d, J=8.67 Hz, 3 H) 7.44-7.49 (m, 2 H) 7.60-7.65 (m, 2 H) 7.68-7.74 (m, 2 H) Calcd for C33H32F9NO2 (M+H) 645.60, Found 646.3.

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
customPurification via Gilson HPLC

Sources & evidence

ORD record: ord-5509288cfc3d4d0a9d16b56884d9e488
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252935B2

Reaction notes

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