1-[5-(2-Ethoxy-2-oxoethoxy)-6-nitropyridin-2-yl]-5-oxopyrrolidin-3-carboxylic acid methyl ester → 5-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-carboxylic acid methyl ester

HRID 1847007ノート

反応式

HRID 1847007 の反応式
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19](OCC)=[O:20])=[C:13]([N+:24]([O-])=O)[N:12]=2)[CH2:6]1)=[O:4]>C(O)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]3[O:17][CH2:18][C:19](=[O:20])[NH:24][C:13]=3[N:12]=2)[CH2:6]1)=[O:4]

参加物

3

反応物 1

HCID 867249371-[5-(2-Ethoxy-2-oxoethoxy)-6-nitropyridin-2-yl]-5-oxopyrrolidin-3-carboxylic acid methyl ester

生成物 1

HCID 867249385-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-carboxylic acid methyl ester収率 84%

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 (55.7 mg, 0.996 mmol) was added to a solution of 1-[5-(2-ethoxy-2-oxoethoxy)-6-nitropyridin-2-yl]-5-oxopyrrolidin-3-carboxylic acid methyl ester (122 mg, 0.332 mmol) in acetic acid (1.2 ml) and the mixture was stirred at 85° C. for 2 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 organic layer was separated, dried over anhydrous magnesium sulfate and then the solvent was removed under reduced pressure to yield 81 mg (84%) 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 organic layer was separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-52087f489c5646dc83d90c40f9ed0711
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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