[(6-{(4S)-4-[(tert-Butoxycarbonyl)amino]-2-oxopyrrolidin-1-yl}-2-nitropyridin-3-yl)oxy]acetic acid ethyl ester → [(3S)-5-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-yl]carbamic acid tert-butyl ester

HRID 1847012노트

반응식

HRID 1847012 반응식
C(O[C:4](=[O:30])[CH2:5][O:6][C:7]1[C:8]([N+:27]([O-])=O)=[N:9][C:10]([N:13]2[CH2:17][C@@H:16]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C:14]2=[O:26])=[CH:11][CH:12]=1)C>C(O)(=O)C>[C:22]([O:21][C:19](=[O:20])[NH:18][C@H:16]1[CH2:15][C:14](=[O:26])[N:13]([C:10]2[CH:11]=[CH:12][C:7]3[O:6][CH2:5][C:4](=[O:30])[NH:27][C:8]=3[N:9]=2)[CH2:17]1)([CH3:25])([CH3:23])[CH3:24]

참가 물질

3

반응물 1

HCID 86724942[(6-{(4S)-4-[(tert-Butoxycarbonyl)amino]-2-oxopyrrolidin-1-yl}-2-nitropyridin-3-yl)oxy]acetic acid ethyl ester

생성물 1

HCID 86724943[(3S)-5-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-yl]carbamic acid tert-butyl ester수율 98%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
85 °C

실험 절차

Reduced iron (150 mg, 2.69 mmol) was added to a solution of [(6-{(4S)-4-[(tert-butoxycarbonyl)amino]-2-oxopyrrolidin-1-yl}-2-nitropyridin-3-yl)oxy]acetic acid ethyl ester (380 mg, 0.895 mmol) in acetic acid (3.8 ml) and the mixture was stirred at 85° C. for 1.5 hours. After cooling, the insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in dichloromethane, a saturated sodium hydrogen carbonate aqueous solution was added thereto and the mixture was stirred for 10 minutes. The solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (chloroform/methanol) to yield 305 mg (98%) of the title compound in the form of a colorless solid.

후처리

  1. temperatureAfter cooling
  2. customthe insoluble material was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane
  5. additiona saturated sodium hydrogen carbonate aqueous solution was added
  6. stirringthe mixture was stirred for 10 minutes
  7. customThe solvent was removed under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

출처 및 근거

ORD 기록
ord-3bc5a3ce871a40b4ab7982456c5f73cd
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952010B2

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