Potassium Hydroxide → HCID 25271448, compound

HRID 889742Notes

Reaction equation

C([O:3][C:4](=[O:45])[CH:5]([C:10]1[CH:11]=[C:12]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[OH-].[K+]>CCO>[CH:22]([N:18]1[CH2:19][CH2:20][CH2:21][CH:16]([C:14]2[CH:15]=[C:10]([CH:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4]([OH:45])=[O:3])[CH:11]=[C:12]([C:35]3[CH:40]=[CH:39][C:38]([C:41]([F:42])([F:43])[F:44])=[CH:37][CH:36]=3)[CH:13]=2)[CH2:17]1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 78 °C

Procedure

To compound 54a, 2-[5-(1-Benzhydryl-piperidin-3-yl)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid ethyl ester (37.8 mg, 0.06 mmol) in EtOH (3.1 ml) was added 2M KOH (0.31 ml, 0.62 mmol). The reaction was heated to 78° C. for 3 hour, cooled to room temperature, and concentrated in vacuo. Purification via Gilson HPLC, salt exchange with 1N HCl (aqueous) gave the product as a white lyophilate, (30 mg, 79%). 1H NMR (300 MHz, MeOD) δ ppm 0.87-0.94 (m, 6 H) 1.37-1.49 (m, J=13.47, 6.64, 6.64, 6.41 Hz, 1 H) 1.63 (dq, J=13.80, 6.95 Hz, 1 H) 1.91-2.01 (m, 3 H) 2.03-2.63 (m, 4 H) 3.05-3.20 (m, 2 H) 3.40-3.55 (m, 1 H) 3.71 (t, J=7.35 Hz, 1 H) 5.43-5.49 (m, 1H) 7.23 (s, 1 H) 7.39-7.55 (m, 8 H) 7.63-7.78 (m, 8 H) Calcd for C37H38F3NO2 (M+H) 585.7, Found 586.3.

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
customPurification via Gilson HPLC, salt exchange with 1N HCl (aqueous)
customgave the product as a white lyophilate, (30 mg, 79%)

Sources & evidence

ORD record: ord-c5461c337b0f43c7a086429fe493b341
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252935B2

Reaction notes

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