[(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 1847012ノート

反応式

HRID 1847012 の反応式
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]

参加物

3

反応物 1

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

生成物 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 ester収率 98%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3bc5a3ce871a40b4ab7982456c5f73cd
出典データセット
uspto-grants-2015_02
特許番号
US08952010B2

反応ノート

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