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

HRID 1414114Notes

Reaction equation

HRID 1414114 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-methyl-enecepham-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-9b5974a0b1594609896b66f1be7784d6
Source dataset
uspto-grants-1981_02
Patent number
US04252950

Reaction notes

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