Potassium Hydroxide → HCID 25271446, compound

HRID 889738Notes

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][N:18]([CH2:22][C:23]3[CH:28]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:26]=[C:25]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:24]=3)[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[OH-].[K+]>CCO>[C:33]([C:25]1[CH:24]=[C:23]([CH:28]=[C:27]([C:29]([CH3:30])([CH3:31])[CH3:32])[CH:26]=1)[CH2:22][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:47])=[O:3])[CH:11]=[C:12]([C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:45])([F:46])[F:44])=[CH:39][CH:38]=3)[CH:13]=2)[CH2:17]1)([CH3:36])([CH3:34])[CH3:35]

Participants

Conditions

Temperature: 78 °C

Procedure

To compound 52a, 2-{5-[1-(3,5-Di-tert-butyl-benzyl)-piperidin-3-yl]-4′-trifluoromethyl-biphenyl-3-yl}-4-methyl-pentanoic acid ethyl ester (85.3 mg, 0.13mmol) in EtOH (6.6 ml) was added 2M KOH (0.66 ml, 1.3 mmol). The reaction was heated to 78° C. for 1 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, (50.0 mg, 58%). 1H NMR (300 MHz, MeOD) δ ppm 0.95 (d, J=6.41 Hz, 6 H) 1.34 (s, 18 H) 1.40-1.56 (m, 1H) 1.61-1.71 (m, 1 H) 1.89-2.14 (m, 5 H) 3.01-3.25 (, 3 H) 3.50-3.61 (m, 2 H) 3.73-3.78 (m, 1H) 4.29-4.40 (m, 2 H) 7.30-7.39 (m, 2 H) 7.48 (s, 1 H) 7.57 (d, J=1.88 Hz, 2 H) 7.73-7.82 (m, 4 H) Calcd for C39H50F3NO2 (M+H) 621.82, Found 622.5.

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, (50.0 mg, 58%)

Sources & evidence

ORD record: ord-a7965bcbf56d4b408e857959e0de2667
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252935B2

Reaction notes

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