Oxygen → 4-Acetylthio-2-azetidinone

HRID 426458

Reaction equation

HRID 426458 reaction equation
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]

Participants

6

Reactant 4

HCID 977Oxygen2×HCID 1199814-Acetoxy-2-azetidinoneHCID 516892Sodium BicarbonateHCID 178418634HCID 178418634, compound

Product 1

HCID 131320584-Acetylthio-2-azetidinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-93b6f3003ddc4a4fad3c42a45db5a384
Source dataset
uspto-grants-1979_10
Patent number
US04169833

Linked notes

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