Diazomethane → HCID 70604184, compound
Reaction equation
[N+:1]([C:4]1[CH:34]=[CH:33][C:7]([CH2:8][O:9][C:10]([C:12]2[N:17]3[C:18](=[O:31])[CH:19]([NH:20][C:21](=[O:30])[CH2:22][O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C@H:16]3[S:15][CH2:14][C:13]=2[OH:32])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+](=[CH2:37])=[N-]>>[O:23]([CH2:22][C:21]([NH:20][CH:19]1[C:18](=[O:31])[N:17]2[C:12]([C:10]([O:9][CH2:8][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:34][CH:33]=3)=[O:11])=[C:13]([O:32][CH3:37])[CH2:14][S:15][C@H:16]12)=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1Participants
Procedure
More recently in my copending application Ser. No. 310,191 filed on Nov. 28, 1972 now U.S. Pat. No. 3,917,587 issued Nov. 4, 1974 the oxidation of 3-exomethylenecepham esters with ozone is described. The predominant product of the ozonolysis described therein is the 3-hydroxy-3-cephem ester which is reacted with a diazoalkene to provide the corresponding ester of a 3-alkoxy-3-cephem. Removal of the ester group provides the alkoxylated antibiotic compound. For example, 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester, obtained by the ozonolysis of the corresponding 3-exomethylene compound, is reacted with diazomethane to form p-nitrobenzyl 7-phenoxyacetamido-3-methoxy-3-cephem4-carboxylate. The p-nitrobenzyl ester group is removed by catalytic hydrogenolysis in the presence of 5% palladium on carbon catalyst to provide the free carboxylic acid antibiotic compound. In the same application Ser. No. 310,191, the formation of 3-exomethylenecepham-4-carboxylic ester sulfoxides and 3-hydroxy-3-cephem-4-carboxylic acid ester sulfoxides are disclosed as side products of the ozonolysis reaction of 3-exomethylenecepham esters.
Workup
- customRemoval of the ester group
- customprovides the alkoxylated antibiotic compound
Sources & evidence
- ORD record
- ord-fbab4d4d04724f43bfef91630b1e3aa2
- Source dataset
- uspto-grants-1977_11
- Patent number
- US04060688
Reaction notes
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