Potassium Hydroxide → HCID 25270775, compound

HRID 889727Notes

Reaction equation

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

Participants

Conditions

Temperature: 78 °C

Procedure

To compound 46a, 4-Methyl-2-[5-(1-naphthalen-2-ylmethyl-piperidin-3-yl)-4′-trifluoromethyl-biphenyl-3-yl]-pentanoic acid ethyl ester (48.4 mg, 0.082mmol) in EtOH (4.1 ml) was added 2M KOH (0.41 ml, 0.82 mmol). The reaction was heated to 78° C. for 1.5 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, (27 mg, 56%). 1HNMR (300 MHz, MeOD) δ ppm 0.88-0.96 (m, 7 H) 1.41-1.52 (m, J=6.59, 6.59, 6.59, 6.59 Hz, 1 H) 1.61-1.70 (m, J=7.06, 6.74, 6.74, 2.45 Hz, 1 H) 1.89-2.02 (m, 3 H) 2.04-2.14 (m, 2 H) 3.08-3.05 (m, 3 H) 3.52-3.67 (m, 2 H) 3.75 (t, J=7.91 Hz, 1 H) 4.47-4.61 (m, 2 H) 7.32 (s, 1 H) 7.49-7.64 (m, 5 H) 7.77 (q, J=8.29 Hz, 4 H) 7.91-8.02 (m, 3 H) 8.07 (s, 1 H), Calcd for C32H32F7NO2 (M+H) 559.66, Found 560.4.

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, (27 mg, 56%)

Sources & evidence

ORD record: ord-0f98797940f9452b9671a620d9f2fd3d
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252935B2

Reaction notes

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