Sodium Hydroxide → Racemic 3-{4-[1-(4'-trifluoromethyl-biphenyl-4-yloxy)-propyl]-benzoylamino}-propionic acid

HRID 1914291Notes

Reaction equation

HRID 1914291 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][NH:6][C:7](=[O:34])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[CH2:15][CH3:16])=[CH:10][CH:9]=1.[OH-].[Na+]>CO>[F:31][C:30]([F:32])([F:33])[C:27]1[CH:26]=[CH:25][C:24]([C:21]2[CH:22]=[CH:23][C:18]([O:17][CH:14]([C:11]3[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:35])=[O:2])=[O:34])=[CH:13][CH:12]=3)[CH2:15][CH3:16])=[CH:19][CH:20]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 671534663-{4-[1-(4'-Trifluoromethyl-biphenyl-4-yloxy)-propyl]-benzoylamino}-propionic acid methyl ester

Product 1

HCID 11554614Racemic 3-{4-[1-(4'-trifluoromethyl-biphenyl-4-yloxy)-propyl]-benzoylamino}-propionic acidYield 95.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 3-{4-[1-(4′-Trifluoromethyl-biphenyl-4-yloxy)-propyl]-benzoylamino}-propionic acid methyl ester (60 mg, 0.12 mmol) in methanol (2 mL) is added sodium hydroxide (5 N aqueous, 0.5 mL) and stirred for 5 hours. The reaction mixture is concentrated and acidified by 5 N HCl (0.5 mL), extracted with ethyl acetate. Combined organic layers are washed with water and brine, dried over sodium sulfate. Concentration gives the title compound (54 mg). MS (ES): 472.2 [M+H]+.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. extractionextracted with ethyl acetate
  3. washCombined organic layers are washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration

Sources & evidence

ORD record
ord-de48ff6aa6454f15a12bd2d24e7f7d5c
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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