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

HRID 1287589Notes

Reaction equation

HRID 1287589 reaction equation
[NH2:1][CH:2]1[C:23](=[O:24])[N:4]2[CH:5]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[O:11])[C:6](=C)[CH2:7][S:8][C@H:3]12.C[OH:26]>>[NH2:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[O:11])=[C:6]([OH:26])[CH2:7][S:8][C@H:3]12

Participants

3

Reactant 2

HCID 887MethanolHCID 68132005HCID 68132005, compound

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 1 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-0a5621be56314307a5a7cc7ed1a11db9
Source dataset
uspto-grants-1976_10
Patent number
US03985737

Reaction notes

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