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

HRID 1730302Notes

Reaction equation

HRID 1730302 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-a4d238b4c85a40488cb84b622cc750ce
Source dataset
uspto-grants-1976_11
Patent number
US03992377

Reaction notes

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