Sodium Hydroxide → 5-((tert-Butoxycarbonyl)amino)-3-methylthiophene-2-carboxylic acid

HRID 446583Notes

Reaction equation

HRID 446583 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:14]([O:16]C)=[O:15])=[C:11]([CH3:18])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:14]([OH:16])=[O:15])=[C:11]([CH3:18])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 58873954Methyl 5-[(tert-butoxycarbonyl)amino]-3-methylthiophene-2-carboxylate

Product 1

HCID 434168385-((tert-Butoxycarbonyl)amino)-3-methylthiophene-2-carboxylic acidYield 71.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

The compound (1.81 g, 6.68 mmol) obtained in Example 30b was dissolved in methanol (27 mL), a 1 N aqueous sodium hydroxide solution (26.7 mL, 26.7 mmol) was added, and the mixture was stirred at 50° C. for 19.5 hours. A 1 N aqueous sodium hydroxide solution (26.7 mL, 26.7 mmol) was added to the reaction mixture, and the mixture was stirred at 50° C. for 24 hours. Methanol was evaporated under reduced pressure, water and ethyl acetate were added to the resulting residue, and the mixture was extracted with water (×2). The resulting aqueous layer was adjusted to pH 1 with 1 N hydrochloric acid, the mixture was extracted with ethyl acetate (×2), and then the organic layer was washed with saturated sodium chloride solution. The organic layer was dried with anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and moisture was removed from the resulting residue azeotropically with toluene (×2) to give the title compound (1.23 g; yield, 62%) as a white solid.

Workup

  1. stirringthe mixture was stirred at 50° C. for 24 hours
  2. customMethanol was evaporated under reduced pressure, water and ethyl acetate
  3. additionwere added to the resulting residue
  4. extractionthe mixture was extracted with water (×2)
  5. extractionthe mixture was extracted with ethyl acetate (×2)
  6. washthe organic layer was washed with saturated sodium chloride solution
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure, and moisture
  9. customwas removed from the resulting residue azeotropically with toluene (×2)

Sources & evidence

ORD record
ord-37408d19d5b646c79129897c8fe5c544
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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