Sodium Hydroxide → HCID 25266921, compound

HRID 889753Notes

Reaction equation

HRID 889753 reaction equation
C([O:3][C:4](=[O:48])[CH:5]([C:10]1[CH:11]=[C:12]([C:38]2[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][N:19]([CH:22]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=3)[CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:18][CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[OH-].[Na+]>CO>[CH3:8][CH:7]([CH3:9])[CH2:6][CH:5]([C:10]1[CH:11]=[C:12]([C:38]2[CH:39]=[CH:40][C:41]([C:44]([F:46])([F:47])[F:45])=[CH:42][CH:43]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][N:19]([CH:22]([C:28]3[CH:29]=[CH:30][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:33]=3)[CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[CH2:18][CH2:17]2)[CH:15]=1)[C:4]([OH:48])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57666001HCID 57666001, compound

Product 1

HCID 25266921HCID 25266921, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of a mixture of 4-methyl-2-(5-{1-[4-methyl-1-(4-trifluoromethyl-phenyl)-pentyl]-piperidin-4-yl}-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester and methyl ester (56 mg, 0.09 mmol) in MeOH (1 mL) was added 3N NaOH (0.060 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 ISCO column chromatography to obtain 4-methyl-2-(5-{1-[4-methyl-1-(4-trifluoromethyl-phenyl)-pentyl]-piperidin-4-yl}-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid.

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 ISCO column chromatography

Sources & evidence

ORD record
ord-94a7ba6fed9f424bb7f3ca00d4be24d8
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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