Hydrogen Peroxide → tert-butyl (6R,7R)-6-(2-amino-2-oxoethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

HRID 1022670ノート

反応式

HRID 1022670 の反応式
[C:1]([CH2:3][C@H:4]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[O:9][CH2:8][CH2:7][N:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:5]1)#[N:2].C(=O)([O-])[O-:27].[K+].[K+].OO.S([O-])([O-])(=O)=S.[Na+].[Na+]>CS(C)=O>[NH2:2][C:1](=[O:27])[CH2:3][C@H:4]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[O:9][CH2:8][CH2:7][N:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:5]1

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 66975920tert-butyl (6R,7R)-6-(cyanomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

生成物 1

HCID 66976771tert-butyl (6R,7R)-6-(2-amino-2-oxoethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate収率 71.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of tert-butyl (6R,7R)-6-(cyanomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (1 g) in DMSO (10 mL) were added potassium carbonate (0.502 g) and 30% aqueous hydrogen peroxide (1.22 mL) at room temperature. The reaction mixture was stirred at room temperature for 1.5 hr. Diluted aqueous sodium thiosulfate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (746 mg).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-d13f28fec89745bda92720aa04f557aa
出典データセット
uspto-grants-2014_05
特許番号
US08722662B2

反応ノート

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