Sodium Hydroxide → HCID 25267285, compound

HRID 889757Notes

Reaction equation

HRID 889757 reaction equation
C([O:3][C:4](=[O:38])[CH:5]([C:10]1[CH:11]=[C:12]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][N:19]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH2:18][CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[OH-].[Na+]>CO>[CH:22]1([N:19]2[CH2:20][CH2:21][CH:16]([C:14]3[CH:15]=[C:10]([CH:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4]([OH:38])=[O:3])[CH:11]=[C:12]([C:28]4[CH:29]=[CH:30][C:31]([C:34]([F:36])([F:37])[F:35])=[CH:32][CH:33]=4)[CH:13]=3)[CH2:17][CH2:18]2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57666011HCID 57666011, compound

Product 1

HCID 25267285HCID 25267285, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of a mixture of 2-[5-(1-cyclohexyl-piperidin-4-yl)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid ethyl ester and methyl ester (50 mg, 0.09 mmol) in MeOH (1 mL) was added 3N NaOH (0.100 mL) and heated to 50° 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-(1-cyclohexyl-piperidin-4-yl)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid. 1H-NMR (DMSO-d6): δ 0.82 (d, 6H), 1.00-1.45 (m, 6H), 1.54 (m, 2H), 1.74-2.06 (m, 9H), 2.83-3.22 (m, 4H), 3.46 (bd, 2H), 3.63 (t, 1H), 7.20 (s, 1H), 7.39 (s, 1H), 7.47 (s, 1H), 7.78 (dd, 4H), 12.35 (bs, 1H); Calcd for C30H38F3NO2 (M+H) 502.62, Found 502.4

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-67169a056c104b4fb7664b7bbf05a9db
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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