Oxygen → 4-Acetylthio-2-azetidinone

HRID 426458

反応式

HRID 426458 の反応式
O=O.[C:3]([OH:6])(=[S:5])[CH3:4].C(O[CH:11]1[NH:14][C:13](=[O:15])[CH2:12]1)(=O)C.C([O-])(O)=O.[Na+]>O>[C:3]([S:5][CH:11]1[NH:14][C:13](=[O:15])[CH2:12]1)(=[O:6])[CH3:4]

参加物

6

反応物 4

HCID 977Oxygen2 回HCID 1199814-Acetoxy-2-azetidinoneHCID 516892Sodium BicarbonateHCID 178418634HCID 178418634、化合物

生成物 1

HCID 131320584-Acetylthio-2-azetidinone

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a cold (0°-5°) oxygen-free 1 N NaOH solution (803 ml.) was added over 20 minutes thioacetic acid (57 ml., 61 g., 0.803 mole). The resulting solution was added in ca 20 minutes to a cold (10°) oxygen-free solution of 4-acetoxyazetidinone (94 g., 0.730 mole) in water (300 ml.). The pH of the resulting solution was immediately adjusted to 7.4 with solid NaHCO3. The cooling bath was removed and the solution was stirred for 2.75 hours. The mixture was then extracted with chloroform, the combined organic extracts washed with water (150 ml.) and dried over sodium sulfate. Concentration on a rotary evaporator left a yellow oil (95.3 g., 90%) which solidified to a yellow solid on cooling and seeding. This solid was found identical (by IR, NMR and TLC) to the product obtained in Preparation 1.

後処理

  1. customThe cooling bath was removed
  2. extractionThe mixture was then extracted with chloroform
  3. washthe combined organic extracts washed with water (150 ml.)
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration
  6. customon a rotary evaporator
  7. waitleft a yellow oil (95.3 g., 90%) which
  8. temperatureon cooling
  9. customobtained in Preparation 1

出典と根拠

ORDレコード
ord-93b6f3003ddc4a4fad3c42a45db5a384
出典データセット
uspto-grants-1979_10
特許番号
US04169833

関連ノート

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