Methyl 6-(2,2-dimethylpropionylamino)-2-nitro-3-(2-oxopyrrolidin-1-yl)-benzoate → methyl 6-(2,2-dimethylpropionylamino)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate

HRID 715987ノート

反応式

HRID 715987 の反応式
[CH3:1][C:2]([CH3:26])([CH3:25])[C:3]([NH:5][C:6]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([N+:16]([O-])=O)[C:9]([N:19]2[CH2:23][CH2:22][CH2:21][C:20]2=O)=[CH:8][CH:7]=1)=[O:4]>C(O)(=O)C.[Fe]>[CH3:1][C:2]([CH3:26])([CH3:25])[C:3]([NH:5][C:6]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[N:16]=[C:20]3[CH2:21][CH2:22][CH2:23][N:19]3[C:9]2=[CH:8][CH:7]=1)=[O:4]

参加物

4

反応物 1

HCID 70982623Methyl 6-(2,2-dimethylpropionylamino)-2-nitro-3-(2-oxopyrrolidin-1-yl)-benzoate2 回

生成物 1

HCID 70983330methyl 6-(2,2-dimethylpropionylamino)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate収率 79.7%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

反応条件

温度
115 °C

実験手順

A mixture of methyl 6-(2,2-dimethylpropionylamino)-2-nitro-3-(2-oxopyrrolidin-1-yl)-benzoate (Intermediate 57, 0.89 g), and iron powder (1.37 g) in acetic acid (25 mL) was stirred and heated at 115° C. for 2.5 hours. After cooling, the mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate and 2M sodium hydroxide solution and filtered through celite. The organic phase was dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 50-100%. The product was repurified by chromatography on silica, eluting with a mixture of methanol and ethyl acetate with a gradient of 0-10% to give methyl 6-(2,2-dimethylpropionylamino)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate (0.616 g) as an off-white solid.

後処理

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. filtration2M sodium hydroxide solution and filtered through celite
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 50-100%
  10. customThe product was repurified by chromatography on silica
  11. washeluting with a mixture of methanol and ethyl acetate with a gradient of 0-10%

出典と根拠

ORDレコード
ord-e2d4b102ca7d4390bc7dcbfc2dac7315
出典データセット
uspto-grants-2015_11
特許番号
US09187494B2

反応ノート

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