Methanol → HCID 13430191, compound

HRID 2119225Notes

Reaction equation

HRID 2119225 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][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:3])[CH3:2].C(Cl)Cl.C[OH:30]>O=[O+][O-].O=O>[C:1]([O:4][C@@H:5]1[N:8]([C:9](=[O:30])[C:10]([O:12][CH3:13])=[O:11])[C:7](=[O:17])[C@H:6]1[NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 13430187HCID 13430187, compound

Product 1

HCID 13430191HCID 13430191, compound

Reagents, catalysts & solvents 2

HCID 977OxygenSolventHCID 24823OzoneSolvent2×

Procedure

Into a solution of 910 mg (2.5 mmol) of methyl 2-((3S,4S)-4-acetoxy-3-t-butyloxycarbonylaminoazetidin-2-on-1-yl)-3-methylbut-2-enoate in 40 ml of methanol, for 120 minutes at -10° C. in a mixture of ozone and oxygen is introduced at a rate of 0.1 mmol of ozone per minute. The obtained crystalline residue is dissolved by addition of 160 ml of methylene chloride and the solution is washed subsequently with 60 ml of a 10% aqueous sodium bisulfite solution and 60 ml of saturated sodium chloride solution. The organic layer is dried over sodium sulfate and dried in vacuo, affording 640 mg of a noncrystalline solid. Recrystallisation from cold methanol furnishes 613 mg (74%) of pure title compound of a melting point of 144° to 146° C. IR spectrum in methylene chloride: 3400, 3000, 1840, 1765, 1720, 1500, 1360, 1220, 1160 and 1040 cm-1.

Workup

  1. washthe solution is washed subsequently with 60 ml of a 10% aqueous sodium bisulfite solution and 60 ml of saturated sodium chloride solution
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. customdried in vacuo

Sources & evidence

ORD record
ord-01760c18c88743859e73ffcc44898e71
Source dataset
uspto-grants-1987_07
Patent number
US04683303

Reaction notes

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