Methanol → HCID 67959327, compound

HRID 1404965Notes

Reaction equation

HRID 1404965 reaction equation
[NH2:1][C:2](=[O:16])[CH:3]([CH3:15])[O:4][C:5]1[C:9]([Br:10])=[CH:8][S:7][C:6]=1[C:11]([O:13]C)=[O:12].CO.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:1][C:2](=[O:16])[CH:3]([CH3:15])[O:4][C:5]1[C:9]([Br:10])=[CH:8][S:7][C:6]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 67959278HCID 67959278, compound

Product 1

HCID 67959327HCID 67959327, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of methyl 3-(2-amino-1-methyl-2-oxoethoxy)-4-bromothiophene-2-carboxylate (634 mg), MeOH (20 mL) and water (0.074 ml) was added potassium carbonate (853 mg), and the mixture was stirred at 65° C. for 1.5 hr. The reaction mixture was concentrated under reduced pressure, the residue was acidified (pH 1) with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from a mixed solvent of Et2O and hexane to give the title compound (444 mg, 73%) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized from a mixed solvent of Et2O and hexane

Sources & evidence

ORD record
ord-8e8af501d2224e5282fa51593f13ea3a
Source dataset
uspto-grants-2014_12
Patent number
US08916549B2

Reaction notes

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