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

HRID 889716Notes

Reaction equation

HRID 889716 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]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=3)(=[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]=[C:27]([C:31]([F:33])([F:32])[F:34])[CH:26]=3)(=[O:24])=[O:23])[CH2:17]2)[CH:15]=1)[C:4]([OH:45])=[O:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 576660754-Methyl-2-{4'-trifluoromethyl-5-[1-(3-trifluoromethyl-benzenesulfonyl)-piperidin-3-yl]-biphenyl-3-yl}-pentanoic acid ethyl ester

Product 1

HCID 252704364-Methyl-2-{4'-trifluoromethyl-5-[1-(3-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 40a, 4-Methyl-2-{4′-trifluoromethyl-5-[1-(3-trifluoromethyl-benzenesulfonyl)-piperidin-3-yl]-biphenyl-3-yl}-pentanoic acid ethyl ester (47.0 mg, 0.072 mmol) in EtOH (4.0 ml) was added 2M KOH (.36 ml, 0.72 mmol). The reaction was heated to 78° C. for 2 hours, cooled to room temperature, and concentrated in vacuo. Purification via Gilson HPLC, gave the product as a white lyophilate. (31.8 mg, 71% ) 1H NMR (300 MHz, MeOD) δ ppm 0.84 (d, J=6.41 Hz, 6 H) 1.36-1.47 (m, J=13.42, 6.97, 6.76, 6.76 Hz, 1 H) 1.50-1.64 (m, J=16.81, 7.11, 3.77, 3.58 Hz, 2 H) 1.76-1.91 (m, 3 H) 2.43 (t, J=10.93 Hz, 2 H) 2.78-2.89 (m, 1 H) 3.63 (t, J=7.72 Hz, 1 H) 3.69-3.78 (m, 2 H) 7.16 (s, 1 H) 7.38 (d, J=19.59 Hz, 2 H) 7.61-7.77 (m, 5 H) 7.88-7.99 (m, 3 H) Calcd for C31H31F6NO4S (M+H) 627.64, Found 628.0.

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-aaf67772e50d4b6eb6e7c4575005898f
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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