Water → 3-Amino-5-cyclopentanecarbonylthiophene-2-carboxylic acid methyl ester

HRID 72216Notes

Reaction equation

HRID 72216 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]([C:11]1[S:12][C:13]([C:23]([CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])=[CH:14][C:15]=1[NH:16]C(=O)C(F)(F)F)=[O:10].O.C(OCC)(=O)C>CO>[CH3:7][O:8][C:9]([C:11]1[S:12][C:13]([C:23]([CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])=[CH:14][C:15]=1[NH2:16])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 866287855-Cyclopentanecarbonyl-3-(2,2,2-trifluoroacetylamino)thiophene-2-carboxylic acid methyl ester

Product 1

HCID 689435563-Amino-5-cyclopentanecarbonylthiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (2.275 g) was added to a solution of 5-cyclopentanecarbonyl-3-(2,2,2-trifluoroacetylamino)thiophene-2-carboxylic acid methyl ester (1.150 g) in methanol (17 mL), and the mixture was stirred at room temperature for 2 h. Water and ethyl acetate were added. The organic phase was separated off, and the aqueous phase was re-extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated. The product with the molecular weight of 253.32 (C12H15NO3S) was obtained in this way; MS (ESI): 254 (M+H+).

Workup

  1. customThe organic phase was separated off
  2. extractionthe aqueous phase was re-extracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe product with the molecular weight of 253.32 (C12H15NO3S) was obtained in this way

Sources & evidence

ORD record
ord-d16f92d6b9044f7c9271b6b766554529
Source dataset
uspto-grants-2014_09
Patent number
US08828991B2

Reaction notes

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