Sulfur Dioxide → (6S)-4-Nitrobenzyl 3-hydroxy-8-oxo-7-(N-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1414124Notes

Reaction equation

HRID 1414124 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:32](=[O:33])[N:13]3[CH:14]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=4)=[O:20])[C:15](=C)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)=[O:35]>C(Cl)Cl>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:32](=[O:33])[N:13]3[C:14]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=4)=[O:20])=[C:15]([OH:35])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 1119Sulfur DioxideHCID 70562111p-Nitrobenzyl 7-phenylacetamido-3-methylenecepham-4-carboxylate

Product 1

HCID 67685788(6S)-4-Nitrobenzyl 3-hydroxy-8-oxo-7-(N-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the ozonization procedures described in Example 9, a solution of 350 mg. of p-nitrobenzyl 7-phenylacetamido-3-methylenecepham-4-carboxylate in 250 ml. of methylene chloride was cooled to -78° C. and was ozonized. The intermediate ozonide was decomposed in situ with sulfur dioxide and the reaction product was recovered and obtained crystalline by extraction with ethyl acetate.

Workup

  1. customthe reaction product was recovered
  2. customobtained crystalline by extraction with ethyl acetate

Sources & evidence

ORD record
ord-f7c07b88729c499b9a8f0ddfa9c430b9
Source dataset
uspto-grants-1981_02
Patent number
US04252950

Reaction notes

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