Sodium Methoxide → Benzyl (2-oxoazetidin-3-yl)carbamate

HRID 1706518Notes

Reaction equation

HRID 1706518 reaction equation
C([N:7]1[CH2:10][CH:9]([NH:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C:8]1=[O:22])(C(OC)=O)=O.C[O-].[Na+]>CO>[CH2:15]([O:14][C:12]([NH:11][CH:9]1[CH2:10][NH:7][C:8]1=[O:22])=[O:13])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 155923071-Methoxalyl-3-benzyloxycarbonylamino-2-azetidinone

Product 1

HCID 12834623Benzyl (2-oxoazetidin-3-yl)carbamateYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Methoxalyl-3-benzyloxycarbonylamino-2-azetidinone (240 mg.) was dissolved in methanol (10 ml.), and sodium methylate (6 mg.) was added to said solution, and then the mixture was heated under reflux for 45 minutes. The methanol was distilled off from the reaction mixture, and the residue was washed with ether to give crude 3-benzyloxycarbonylamino-2-azetidinone (126 mg.). Furthermore, this product was recrystallized from acetone to give the purified compound (50 mg.). And, the purified same compound (54 mg.) was recovered from the mother liquor. Total yield was 104 mg. Mp 164° to 165° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 45 minutes
  3. distillationThe methanol was distilled off from the reaction mixture
  4. washthe residue was washed with ether

Sources & evidence

ORD record
ord-6b5e221a9b374436ac5b4c5cb810331c
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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