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

HRID 889688Notes

Reaction equation

HRID 889688 reaction equation
C([O:3][C:4](=[O:34])[CH:5]([C:10]1[CH:11]=[C:12]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[CH:13]=[C:14]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[CH2:22][CH3:23])[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[OH-].[Na+]>CO>[CH2:22]([CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][N:16]1[C:14]1[CH:15]=[C:10]([CH:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[C:4]([OH:34])=[O:3])[CH:11]=[C:12]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=2)[CH:13]=1)[CH3:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57665995HCID 57665995, compound

Product 1

HCID 252679802-[5-(2-Ethyl-piperidin-1-yl)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-[5-(2-ethyl-piperidin-1-yl)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid ethyl ester (12 mg, 0.03 mmol) in MeOH (1 mL) was added 3N NaOH (0.200 mL) and heated to 60° C. for 2 h. The reaction was concentrated in vacuo to remove MeOH. The thick liquid was acidified to pH=2 by 2N HCl. The resulting acidic solution was extracted with EtOAc. The organic fraction was dried (MgSO4) and concentrated in vacuo. The crude mixture was purified by Gilson reverse phase column chromatography to obtain 2-[5-(2-ethyl-piperidin-1-yl)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid. 1H-NMR (CDCl3): δ 0.80 (t, 3H), 0.92 (d, 6H), 1.44 (m, 1H), 1.50 (q, 1H), 1.58-1.69 (m, 3H), 1.89 (m, 1H), 2.02 (m, 2H), 2.14-2.26 (m, 2H), 3.29 (m, 2H), 3.68-3.81 (m, 2H), 7.59-7.73 (m, 7H); Calcd for C26H32F3NO2 (M+H) 448.53, Found 448.34

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customto remove MeOH
  3. extractionThe resulting acidic solution was extracted with EtOAc
  4. dry with materialThe organic fraction was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was purified by Gilson reverse phase column chromatography

Sources & evidence

ORD record
ord-cca413837bd8468697e5f7ace4b06c6d
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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