Methanol → 4-Nitrobenzyl 7-amino-3-hydroxy-3-cephem-4-carboxylate

HRID 443529Notes

Reaction equation

HRID 443529 reaction equation
Cl.[NH2:2][CH:3]1[C:24](=[O:25])[N:5]2[CH:6]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[O:12])[C:7](=C)[CH2:8][S:9][C@H:4]12.C[OH:27]>>[NH2:2][CH:3]1[C:24](=[O:25])[N:5]2[C:6]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[O:12])=[C:7]([OH:27])[CH2:8][S:9][C@H:4]12

Participants

3

Reactant 2

HCID 887MethanolHCID 70560152p-Nitrobenzyl 7-amino-3-methylenecepham-4-carboxylate hydrochloride

Product 1

HCID 681232354-Nitrobenzyl 7-amino-3-hydroxy-3-cephem-4-carboxylate

Procedure

In a further example, p-nitrobenzyl 7-amino-3-methylenecepham-4-carboxylate hydrochloride is dissolved in methanol and ozone is bubbled through the solution at a temperature of about -78° C. Excess ozone is purged from the mixture with nitrogen and the ozonide is decomposed by bubbling sulfur dioxide through the mixture. The reaction mixture is evaporated to dryness and the residue, p-nitrobenzyl 7-amino-3-hydroxy-3-cephem-4-carboxylate is obtained as the hydrochloride salt.

Workup

  1. customozone is bubbled through the solution at a temperature of about -78° C
  2. customExcess ozone is purged from the mixture with nitrogen
  3. customby bubbling sulfur dioxide through the mixture
  4. customThe reaction mixture is evaporated to dryness

Sources & evidence

ORD record
ord-7e4532b93b444cd0855cd87bf4c3d3dc
Source dataset
uspto-grants-1981_04
Patent number
US04260745

Reaction notes

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