Hydrogen Peroxide → allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1464736ノート

反応式

HRID 1464736 の反応式
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[C@@H:6]([CH3:20])[C:7]([S:18][CH3:19])=[C:8]2[C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])[CH3:3].[OH:21]O>C(O)C.C(Cl)Cl>[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[C@@H:6]([CH3:20])[C:7]([S:18]([CH3:19])=[O:21])=[C:8]2[C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])[CH3:3]

参加物

5

反応物 2

HCID 784Hydrogen PeroxideHCID 57069192allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

生成物 1

HCID 57058048allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (100 mg) in ethanol (1.0 ml) was added a 30% aqueous solution of hydrogen peroxide (0.5 ml) and the mixture was allowed to stand at the ambient temperature for 18 hours. The solution was diluted with methylene dichloride and washed with water, 5% aqueous sodium thiosulfate solution and brine successively. The organic layer was dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (50.0 mg).

後処理

  1. washwashed with water, 5% aqueous sodium thiosulfate solution and brine successively
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-44597d8ad9a847b8a662f6b34496c7c5
出典データセット
uspto-grants-1994_04
特許番号
US05306816

反応ノート

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