Potassium Carbonate → HCID 22010261, compound

HRID 322900Notes

Reaction equation

HRID 322900 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][CH:8]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH3:38])[O:9][C:10]1[CH:24]=[C:23]([O:25][CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[CH:22]=[CH:21][C:11]=1[C:12]([NH:14][C:15](=[CH2:20])[C:16]([O:18]C)=[O:17])=[O:13])=[O:5])C.C(=O)([O-])[O-].[K+].[K+]>CO>[C:4]([CH2:6][CH2:7][CH:8]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH3:38])[O:9][C:10]1[CH:24]=[C:23]([O:25][CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[CH:22]=[CH:21][C:11]=1[C:12]([NH:14][C:15](=[CH2:20])[C:16]([OH:18])=[O:17])=[O:13])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86756588HCID 86756588, compound

Product 1

HCID 22010261HCID 22010261, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (RS)-2-[2-(3-ethoxycarbonyl-1-(2-methylphenyl)propoxy)-4-(3-thienylmethoxy)benzoylamino]acrylate (200 mg) in methanol (20 mL) containing 10% w/v potassium carbonate (2 mL) is stirred at ambient temperature for 16 hours and at reflux for 3 hours. The reaction mixture is partitioned between 1N HCl (50 mL) and ethyl acetate (50 mL) then the organic phase is washed with water (2×50 mL), dried over magnesium sulphate, filtered and concentrated under reduced pressure. Recrystallisation from cyclohexane/ethyl acetate gives (RS)-2-[2-(3-carboxy-1-(2-methylphenyl)propoxy)-4-(3-thienylmethoxy)benzoylamino]acrylic acid as a white, fluffy solid (20 mg), m.p. 140-143° C. [Elemental analysis:- C,61.9, H, 5.32, N, 2.53%. Calculated:- C,61.9, H, 5.16, N, 2.78%]

Workup

  1. temperatureat reflux for 3 hours
  2. customThe reaction mixture is partitioned between 1N HCl (50 mL) and ethyl acetate (50 mL)
  3. washthe organic phase is washed with water (2×50 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-488a9bcb07a84960bac5f81027c86fae
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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