Potassium Hydroxide → HCID 25268342, compound

HRID 889692Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To 4-Methyl-2-[5-(6-methyl-piperidin-2-yl)-4′-trifluoromethyl-biphenyl-3-yl]-pentanoic acid ethyl ester, compounds 6c in EtOH (4 mL) was added 2M KOH (162 μL, 0.324 mmol). The reaction was heated to 80° C. for 2 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. 1H NMR (300 MHz, MeOD) δ ppm 0.96 (dd, J=6.59, 1.70 Hz, 6 H) 1.39 (d, J=6.41 Hz, 3 H) 1.49-1.63 (m, 2 H) 1.65-1.80 (m, 1 H) 1.85 (d, J=4.14 Hz, 1 H) 2.06 (dt, J=13.56, 7.72 Hz, 5 H) 3.35-3.49 (m, 1 H) 3.83 (t, J=7.72 Hz, 1 H) 4.36 (dd, J=12.06, 2.64 Hz, 1 H) 7.53-7.57 (m, 1 H) 7.73 (s, 2 H) 7.76-7.88 (m, 4 H) Calcd for C25H30F3NO2 (M+H) 433.51, Found 434.2.

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
customPurification via Gilson HPLC

Sources & evidence

ORD record: ord-2a8422cb39d54c57b73d11f056013d30
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252935B2

Reaction notes

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