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

HRID 446583노트

반응식

HRID 446583 반응식
[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]

참가 물질

4

반응물 2

HCID 14798Sodium Hydroxide2회HCID 58873954Methyl 5-[(tert-butoxycarbonyl)amino]-3-methylthiophene-2-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-37408d19d5b646c79129897c8fe5c544
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476253B2

반응 노트

불러오는 중…