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 1278351Notes

Reaction equation

HRID 1278351 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-a5680442cacb4801bb159b2474e01ac2
Source dataset
uspto-grants-1981_07
Patent number
US04281116

Reaction notes

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