Potassium Carbonate → 4-(2-Methylphenyl)butanoic acid hydrate

HRID 322897Notes

Reaction equation

HRID 322897 reaction equation
[O:1]1CCN=C1C1C=CC(OCC2C=CSC=2)=CC=1O[CH:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])[CH2:10][CH2:11][C:12]([O:14]CC)=[O:13].C(=O)([O-])[O-].[K+].[K+]>CO>[OH2:1].[CH3:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 10624529HCID 10624529, compound

Product 1

HCID 867565874-(2-Methylphenyl)butanoic acid hydrateYield 78.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl (RS)-4-[2-(4,5-dihydrooxazol-2-yl)-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate (500 mg) in methanol (50 mL) containing 10% w/v potassium carbonate (5 mL) is stirred at ambient temperature for 16 hours. The reaction mixture is concentrated under reduced pressure and partitioned between water (100 mL) and ethyl acetate (100 mL) then acidified to pH 5 with 1 N HCl. The organic phase is washed three times with water (50 mL), dried over magnesium sulphate, filtered and concentrated under reduced pressure. Recrystallisation from cyclohexane/ethyl acetate gives (RS)-4-[2-(4,5-dihydrooxazol-2-yl))-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoic acid hydrate as a white solid (160 mg), m.p. 107-109° C. [Elemental analysis:- C,65.9, H, 5.69, N, 2.94%. Calculated for C25H25NO5S.0.2H2O:- C,66.0, H, 5.59, N, 3.01%].

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. custompartitioned between water (100 mL) and ethyl acetate (100 mL)
  3. washThe organic phase is washed three times with water (50 mL)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customRecrystallisation from cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-fe129453d2b94b8da9c31aa5ac0fb3ce
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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