Carbon Dioxide → 3-((tert-Butoxycarbonyl)amino)furan-2-carboxylic acid

HRID 32594

반응식

HRID 32594 반응식
C([Li])CCC.[O:6]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:7]1.[C:19](=[O:21])=[O:20]>C1COCC1.C(OCC)C.O>[C:14]([O:13][C:12]([NH:11][C:8]1[CH:9]=[CH:10][O:6][C:7]=1[C:19]([OH:21])=[O:20])=[O:18])([CH3:15])([CH3:17])[CH3:16]

참가 물질

7

반응물 3

HCID 280Carbon DioxideHCID 12207186tert-butyl N-(furan-3-yl)carbamate2회HCID 178418339Butyllithium

생성물 1

HCID 468356103-((tert-Butoxycarbonyl)amino)furan-2-carboxylic acid

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
-40 °C

실험 절차

Butyl lithium (as 1.6 M in hexanes, 45 mL) was added slowly to a solution of tert-butyl 3-furylcarbamate (Intermediate 80) (5.49 g) in THF (60 mL) at −40° C., keeping the internal reaction temperature less than −35° C. The reaction was stirred at −40° C. for 4 hours, then poured onto solid CO2 (100 mL) under a blanket of diethyl ether (300 mL). After warming to ambient temperature, the mixture was poured into water (300 mL) with stirring and an additional 100 mL diethyl ether added. The phases were separated and the organic phase was further extracted into water (2×100 mL). The combined organic phases were washed with ether, acidified by addition of aqueous HCl, and extracted into EtOAc (4×250 mL). The combined extracts were dried and evaporated to give a pale yellow solid (7.5 g). This was triturated with cyclohexane to afford the title compound as a white solid (4.80 g, 70%);

후처리

  1. customthe internal reaction temperature less than −35° C
  2. temperatureAfter warming to ambient temperature
  3. stirringwith stirring
  4. customThe phases were separated
  5. extractionthe organic phase was further extracted into water (2×100 mL)
  6. washThe combined organic phases were washed with ether
  7. additionacidified by addition of aqueous HCl
  8. extractionextracted into EtOAc (4×250 mL)
  9. customThe combined extracts were dried
  10. customevaporated

출처 및 근거

ORD 기록
ord-679b5132f25e4af88d4f6adc1ee7faa2
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427616B2

연결된 노트

불러오는 중…