Potassium Hydroxide → 2-[5-(1-Methanesulfonyl-piperidin-3-yl)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid

HRID 889714Notes

Reaction equation

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

Participants

Conditions

Temperature: 78 °C

Procedure

To a solution of compound 39a, 2-[5-(1-Methanesulfonyl-piperidin-3-yl)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid ethyl ester (70.0 mg, 0.133 mmol) in EtOH (6.5 ml) was added 2M KOH (0.027 ml, 0.53 mmol). The reaction was heated to 78° C. for 3 hours, cooled to room temperature, and concentrated in vacuo. Purification via Gilson HPLC, gave the product as a white lyophilate. (53.4 mg, 81%) 1H NMR (300 MHz, MeOD) δ ppm 0.85 (dd, J=6.59, 1.70 Hz, 6 H) 1.42 (dt, J=13.28, 6.74 Hz, 1 H) 1.56-1.71 (m, 3 H) 1.79-1.87 (m, 1 H) 1.92 (dd, J=13.56, 7.16 Hz, 2 H) 2.69-2.85 (m, 5 H) 3.19-3.23 (m, 2 H) 3.61-3.72 (m, 3 H) 7.23 (s, 1 H) 7.42 (d, J=1.51 Hz, 2 H) 7.62-7.74 (m, 4 H) Calcd for C25H30F3NO4S (M+H) 497.57, Found 498.3.

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
customPurification via Gilson HPLC
customgave the product as a white lyophilate

Sources & evidence

ORD record: ord-d3ce2704dafb433d948d9eec5f4a86a1
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252935B2

Reaction notes

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