Dimethylformamide → 3-Acetylthio-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine

HRID 37015ノート

反応式

HRID 37015 の反応式
CN(C)C=O.[H-].[Na+].[C:8]([OH:11])(=[S:10])[CH3:9].CS(O[CH:17]1[CH2:21][CH2:20][N:19]([C:22](=[N:24][C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=2)=[O:26])[CH3:23])[CH2:18]1)(=O)=O>O>[C:8]([S:10][CH:17]1[CH2:21][CH2:20][N:19]([C:22](=[N:24][C:25]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=2)=[O:26])[CH3:23])[CH2:18]1)(=[O:11])[CH3:9]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 539971713-Methanesulphonyloxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidineHCID 178418634HCID 178418634、化合物

生成物 1

HCID 540371453-Acetylthio-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine収率 79.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To 300 ml of anhydrous N,N-dimethylformamide were added 7.35 g of sodium hydride in the form of a 55% w/w/ dispersion in oil, followed by 12.5 g of thioacetic acid. The mixture was then stirred for 10 minutes, with ice-cooling, after which 40 g of 3-methanesulphonyloxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine were added. The mixture was then stirred for 3 hours at 65° C. After the reaction mixture had been allowed to cool, water was added and the mixture was extracted with ethyl acetate. The extract was washed with water and dried and then the solvent was distilled off under reduced pressure. The residue was purified by chromatography through a column of silica gel, eluted with a 2:1 by volume mixture of benzene and ethyl acetate, to give 30 g of the title compound.

後処理

  1. temperaturecooling
  2. stirringThe mixture was then stirred for 3 hours at 65° C
  3. temperatureto cool
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by chromatography through a column of silica gel
  9. washeluted with a 2:1 by volume mixture of benzene and ethyl acetate

出典と根拠

ORDレコード
ord-10b960678bc34a7c81eff1c395c66e14
出典データセット
uspto-grants-1995_05
特許番号
USRE034960

反応ノート

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