Oxygen → HCID 13430189, compound

HRID 2119227Notes

Reaction equation

HRID 2119227 reaction equation
[C:1]([O:4][C@@H:5]1[N:8]([C:9](=C(C)C)[C:10]([O:12][CH3:13])=[O:11])[C:7](=[O:17])[C@H:6]1[NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])(=[O:3])[CH3:2].[O:29]=[O+][O-].O=O>CO.C(Cl)Cl>[C:1]([O:4][C@@H:5]1[N:8]([C:9](=[O:29])[C:10]([O:12][CH3:13])=[O:11])[C:7](=[O:17])[C@H:6]1[NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 977OxygenHCID 24823OzoneHCID 13124489HCID 13124489, compound

Product 1

HCID 13430189HCID 13430189, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Into a solution of 970 mg (2.5 mmol) methyl 2-((3S,4S)-4-acetoxy-3-benzyloxycarbonylaminoazetidin-2-on-1-yl)-3-methylbut-2-enoate in 40 ml of methanol, at -10° C., for 120 minutes a mixture of ozone and oxygen is introduced at a rate of 0.1 mmol per minute. The clear solution is diluted with 60 ml of methylene chloride and the mixture subsequently washed with 50 ml of aqueous sodium bisulfite solution (10%) and 100 ml of saturated sodium chloride solution. After drying of the organic layer over sodium sulfate, filtration and evaporation of the filtrate in vacuo 780 mg of a noncrystalline solid is obtained (86%) (title compound). IR spectrum in methylene chloride: 3400, 1835, 1755, 1720 and 1510 cm-1.

Workup

  1. additionis introduced at a rate of 0.1 mmol per minute
  2. washthe mixture subsequently washed with 50 ml of aqueous sodium bisulfite solution (10%) and 100 ml of saturated sodium chloride solution
  3. dry with materialAfter drying of the organic layer over sodium sulfate, filtration and evaporation of the filtrate in vacuo 780 mg of a noncrystalline solid

Sources & evidence

ORD record
ord-146588da5e304ab09eeca2b6f158f78f
Source dataset
uspto-grants-1987_07
Patent number
US04683303

Reaction notes

Loading…