Sodium Methoxide → HCID 15592308, compound

HRID 1706517Notes

Reaction equation

HRID 1706517 reaction equation
C[O-].[Na+].C([N:10]1[CH2:13][CH:12]([NH:14][C:15](=[O:24])[CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11]1=[O:25])(C(OC)=O)=O>CO>[O:17]([CH2:16][C:15]([NH:14][CH:12]1[CH2:13][NH:10][C:11]1=[O:25])=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 70513826HCID 70513826, compound

Product 1

HCID 15592308HCID 15592308, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methylate (15 mg.) and absolute methanol (20 ml.) were added to 1-methoxalyl-3-(2-phenoxyacetamido)-2-azetidinone (1.1 g.), and the mixture was heated under reflux for 30 minutes. The solvent was distilled off from the reaction mixture under reduced pressure, and the residue was dissolved in acetone, and then the insoluble material was filtered off. The filtrate was concentrated and allowed to stand cool, and then the precipitated crystals were collected by filtration. The crystals were washed with acetone and dried to give 3-(2-phenoxyacetamido)-2-azetidinone (456 mg.). Furthermore, the same compound (109 mg.) was recovered from the mother liquor. Total yields was 565 mg. Mp 153° to 155° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. distillationThe solvent was distilled off from the reaction mixture under reduced pressure
  4. dissolutionthe residue was dissolved in acetone
  5. filtrationthe insoluble material was filtered off
  6. concentrationThe filtrate was concentrated
  7. temperatureto stand cool
  8. filtrationthe precipitated crystals were collected by filtration
  9. washThe crystals were washed with acetone
  10. customdried

Sources & evidence

ORD record
ord-b81410a908b64cb6967e6740f3b77e49
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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