Acetic-formic anhydride → (6R,7R)-2,2-dimethyl-7-formamido-1-aza-3-oxabicyclo[4.2.0]octan-8-one

HRID 235734ノート

反応式

HRID 235734 の反応式
[NH2:1][C@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[CH2:4][CH2:5][O:6][C:7]2([CH3:12])[CH3:11].[CH:13](OC(=O)C)=[O:14]>N1C=CC=CC=1>[CH3:11][C:7]1([CH3:12])[O:6][CH2:5][CH2:4][C@H:3]2[N:8]1[C:9](=[O:10])[C@@H:2]2[NH:1][CH:13]=[O:14]

参加物

4

反応物 2

HCID 75269Acetic-formic anhydrideHCID 12804734(6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one

生成物 1

HCID 54090364(6R,7R)-2,2-dimethyl-7-formamido-1-aza-3-oxabicyclo[4.2.0]octan-8-one

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

To a solution of (6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one (300 mg) were added pyridine (0.25 ml) and freshly prepared acetic formic anhydride (0.38 ml) at 0° C. After stirring for 45 minutes at 0° C., the reaction mixture was evaporated in vacuo. The residue was dissolved in xylene and the solution was evaporated in vacuo. The residue was chromatographed on silica gel (6 g) eluting with a mixture of methylene chloride and methanol (25:1-10:1) to give (6R,7R)-2,2-dimethyl-7-formamido-1-aza-3-oxabicyclo[4.2.0]octan-8-one (378 mg) as an oil.

後処理

  1. customthe reaction mixture was evaporated in vacuo
  2. dissolutionThe residue was dissolved in xylene
  3. customthe solution was evaporated in vacuo
  4. customThe residue was chromatographed on silica gel (6 g)
  5. washeluting with a mixture of methylene chloride and methanol (25:1-10:1)

出典と根拠

ORDレコード
ord-cbebe046f2a34ca38b1922669123d56a
出典データセット
uspto-grants-1987_02
特許番号
US04640915

反応ノート

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