Sodium Hydroxide → HCID 11526712, compound

HRID 1669260Notes

Reaction equation

HRID 1669260 reaction equation
CO[C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C@H:11]([C:19]2[CH:20]=[N:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:6][CH:5]=1.[OH-:36].[Na+]>C(O)C>[CH:13]1([CH2:12][C@@H:11]([C:19]2[CH:20]=[N:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[O:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([NH:21][CH2:20][CH2:19][C:11]([OH:10])=[O:36])=[O:35])=[CH:9][CH:8]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67342848HCID 67342848, compound

Product 1

HCID 11526712HCID 11526712, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

or (S)-4-{2-cyclohexyl-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy}-benzoic acid methyl ester (85 mg) is taken into ethanol (2 mL), treated with 5N NaOH (1 mL) for 2 h at 40° C., concentrated, acidified with 5 N HCl, extracted with ethyl acetate, dried over sodium sulfate. Concentration gives 80 mg of (R) or (S)-4-{2-cyclohexyl-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy}-benzoic acid.

Workup

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration

Sources & evidence

ORD record
ord-5aa6dbfccb3b47b8939fd1638e368533
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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