Potassium Hydroxide → HCID 25268704, compound

HRID 889704Notes

Reaction equation

C([O:3][C:4](=[O:37])[CH:5]([C:10]1[CH:11]=[C:12]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][N:17]2[CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[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:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:29][CH:28]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][N:17]2[CH2:22][CH2:23][CH:24]([CH3:25])[CH3:26])[CH:15]=1)[C:4]([OH:37])=[O:3]

Participants

Conditions

Temperature: 78 °C

Procedure

To a solution of 4-Methyl-2-{5-[1-(3-methyl-butyl)-piperidin-2-yl]-4′-trifluoromethyl-biphenyl-3-yl}-pentanoic acid ethyl ester, compound 10c (32.0 mg, 0.06 mmol)in EtOH (3 mL) was added 2M KOH (130 μl, 0.25 mmol). The reaction was heated to 78° C. for 2 hours, cooled to room temperature, and concentrated in vacuo. Purification via Gilson HPLC, followed by salt exchange with aqueous 1N HCl, followed by lyophilization gave the title compound as a white solid. (12.0 mg, 40%) 1H NMR (300 MHz, MeOD) δ ppm 0.70-0.77 (m, 6 H) 0.90-0.98 (m, 6 H) 1.32 (dt, J=11.59, 5.70 Hz, 1 H) 1.46-1.55 (m, 1 H) 1.63 (td, J=11.59, 6.22 Hz, 1 H) 1.71-1.87 (m, 2 H) 1.98-2.11 (m, 4 H) 2.13-2.18 (m, 1 H) 2.81-2.97 (m, 2 H) 3.22 (td, J=12.15, 3.96 Hz, 1 H) 3.71-3.87 (m, 2 H) 4.32-4.42 (m, 1 H) 7.54-7.60 (m, 1 H) 7.75-7.89 (m, 6 H) Calcd for C29H38F3NO2 (M+H) 489.61, Found 490.0.

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
customPurification via Gilson HPLC

Sources & evidence

ORD record: ord-ddda95b2f06840eb8c59b62fb2781029
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252935B2

Reaction notes

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