Potassium Hydroxide → 4-Methyl-2-{4'-trifluoromethyl-5-[1-(2-trifluoromethyl-benzenesulfonyl)-piperidin-3-yl]-biphenyl-3-yl}-pentanoic acid

HRID 889720Notes

Reaction equation

HRID 889720 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]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])(=[O:24])=[O:23])[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:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:42])[F:43])=[CH:37][CH:36]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:33])([F:32])[F:34])(=[O:24])=[O:23])[CH2:17]2)[CH:15]=1)[C:4]([OH:45])=[O:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 576660064-Methyl-2-{4'-trifluoromethyl-5-[1-(2-trifluoromethyl-benzenesulfonyl)-piperidin-3-yl]-biphenyl-3-yl}-pentanoic acid ethyl ester

Product 1

HCID 252704384-Methyl-2-{4'-trifluoromethyl-5-[1-(2-trifluoromethyl-benzenesulfonyl)-piperidin-3-yl]-biphenyl-3-yl}-pentanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of compound 42a, 4-Methyl-2-{4′-trifluoromethyl-5-[1-(2-trifluoromethyl-benzenesulfonyl)-piperidin-3-yl]-biphenyl-3-yl}-pentanoic acid ethyl ester (34.0 mg, 0.052 mmol) in EtOH (2.6 ml) was added 2M KOH (0.26 ml, 0.52 mmol). The reaction was heated to 78° C. for 1.5 hours, cooled to room temperature, and concentrated in vacuo. Purification via Gilson HPLC, gave the product as a white lyophilate. (17.3 mg, 53%) 1HNMR(300 MHz, MeOD) δ ppm0.79-0.87 (m, 6 H) 1.41 (dt,J=13.28, 6.74 Hz, 1 H) 1.53-1.69 (m, 3 H) 1.79 (dd, J=5.84, 2.83 Hz, 1 H) 1.84-1.96 (m, 2 H) 2.71-2.84 (m, 3 H) 3.64 (t, J=7.72 Hz, 1 H) 3.79 (d, J=6.03 Hz, 2 H) 7.18 (s, 1H) 7.38 (d, J=16.58 Hz, 2 H) 7.62-7.76 (m, 6 H) 7.85-7.90 (m, 1 H) 7.99-8.04 (m, 1 H) Calcd for C31H31F6NO4S (M+H) 627.64, Found 628.3.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customPurification via Gilson HPLC
  4. customgave the product as a white lyophilate

Sources & evidence

ORD record
ord-84a54c3da5bd4e67adf6d9e58ebe2a00
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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