7-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acid → 7-(2-Methoxyimino-3,3-ethylenedioxy-butyramido)-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 1982037Notes

Reaction equation

HRID 1982037 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:8]1([O:13][CH2:12][CH2:11][O:10]1)[CH3:9])[C:5]([OH:7])=O.[NH2:14][CH:15]1[C:32](=[O:33])[N:17]2[C:18]([C:29]([OH:31])=[O:30])=[C:19]([CH2:22][S:23][C:24]3[S:25][CH:26]=[N:27][N:28]=3)[CH2:20][S:21][C@H:16]12>>[CH3:1][O:2][N:3]=[C:4]([C:8]1([O:13][CH2:12][CH2:11][O:10]1)[CH3:9])[C:5]([NH:14][CH:15]1[C:32](=[O:33])[N:17]2[C:18]([C:29]([OH:31])=[O:30])=[C:19]([CH2:22][S:23][C:24]3[S:25][CH:26]=[N:27][N:28]=3)[CH2:20][S:21][C@H:16]12)=[O:7]

Participants

3

Reactant 2

HCID 128891877-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acidHCID 544524052-Methoxyimino-3,3-ethylenedioxybutyric acid

Product 1

HCID 1317125307-(2-Methoxyimino-3,3-ethylenedioxy-butyramido)-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acidYield 81.2%

Procedure

2-Methoxyimino-3,3-ethylenedioxybutyric acid (syn isomer, 15.1 g. ) and 7-amino-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (29.1 g.) were treated in a similar manner to that of Example 10-(2) to give 7-(2-methoxyimino-3,3-ethylenedioxybutyramido)-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 32.5 g.). Mp. 145° to 152° C. (dec.).

Sources & evidence

ORD record
ord-7b21017f45ff4cda9703d9a1166de83b
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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