Sodium Hydroxide → HCID 57709112, compound

HRID 547007Notes

Reaction equation

HRID 547007 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:42])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH2:38][CH3:39])([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]4([OH:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[C:24]([CH3:37])[CH:23]=3)[CH2:20][CH3:21])=[CH:15][C:14]=2[CH3:40])=[CH:9][C:8]=1[F:41].[Cl-].[NH4+]>CO>[CH2:20]([C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:11]=[CH:12][C:7]([CH2:6][C:5]([OH:42])=[O:4])=[C:8]([F:41])[CH:9]=2)=[C:14]([CH3:40])[CH:15]=1)([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]2([OH:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[C:24]([CH3:37])[CH:23]=1)[CH2:38][CH3:39])[CH3:21]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 57709197HCID 57709197, compound

Product 1

HCID 57709112HCID 57709112, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2 N sodium hydroxide aqueous solution (0.3 mL) was added to a solution of [4′-(1-ethyl-1-{4-[2-(1-hydroxy-cyclohexyl)-ethyl]-3-methyl-phenyl}-propyl)-3-fluoro-2′-methyl-biphenyl-4-yl]-acetic acid methyl ester (Example 115-(1); 45.6 mg, 0.0837 mmol) in methanol (0.8 mL), and the mixture was stirred for five hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by thin layer silica gel chromatography (3% methanol/dichloromethane) to give the title compound (34.1 mg, 76%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by thin layer silica gel chromatography (3% methanol/dichloromethane)

Sources & evidence

ORD record
ord-e70e7fc9a9a84735b372513939b22bc5
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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