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

HRID 1902514Notes

Reaction equation

HRID 1902514 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[CH:14]([C:23]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=4)=[O:24])[C:15](=COC(=O)C)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OCC)(=[O:40])C.O=[O+][O-]>CO>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:23]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=4)=[O:24])=[C:15]([OH:40])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24823OzoneHCID 70524504HCID 70524504, compound

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 887MethanolSolvent

Procedure

A solution of 4-nitrobenzyl 7-(2-phenylacetamido)-3-acetoxymethylenecepham-4-carboxylate (1.97 g), ethyl acetate (30 ml) and methanol (7.5 ml) was treated with ozone in a similar manner to that of Example 1 (4) to give 4-nitrobenzyl 7-(2-phenylacetamido)-3-hydroxy-3cephem-4-carboxylate (400 mg.).

Sources & evidence

ORD record
ord-62d4a1bf756a49e9bdd712f4d5f76e15
Source dataset
uspto-grants-1982_12
Patent number
US04363807

Reaction notes

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