Diazomethane → HCID 70604184, compound

HRID 1439793Notes

Reaction equation

HRID 1439793 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:33](=[O:34])[N:14]2[C:15]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)=[O:21])=[C:16]([OH:19])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH2:37])=[N-]>>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:33](=[O:34])[N:14]2[C:15]([C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=3)=[O:21])=[C:16]([O:19][CH3:37])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 9550DiazomethaneHCID 67616247p-Nitrobenzyl 3-hyroxy-7-phenoxyacetamido-3-cephem-4-carboxylate

Product 1

HCID 70604184HCID 70604184, compound

Procedure

The 3-hydroxy-3-cephem ester can then be converted to a 3-alkoxy-3-cephem ester or to a 3-halo-3-cephem ester. For example, 4-nitrobenzyl 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate is allowed to react in an inert solvent with diazomethane to form 4-nitrobenzyl 7-phenoxyacetamido-3-methoxy-3-cephem-4-carboxylate. The 4-nitrobenzyl group is removed by catalytic hydrogenolysis over palladium on carbon catalyst to provide the antibiotic compound 7-phenoxyacetamido-3-methoxy-3-cephem-4-carboxylic acid. These 3-methoxy-3-cephem compounds are highly active antibiotics and are fully disclosed in my copending applications Ser. Nos. 310,190 and 310,191, filed Nov. 28. 1972 now U.S. Pat. Nos. 3,917,588 and 3,917,587, respectively, both issued Nov. 4, 1975.

Sources & evidence

ORD record
ord-0f956d7a978b4b86a00218f630ea7b3c
Source dataset
uspto-grants-1977_11
Patent number
US04060688

Reaction notes

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