3-Carbamoyloxymethyl-7-amino-3-cephem-4-carboxylic acid → 7-[2-Methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

HRID 444276Notes

Reaction equation

HRID 444276 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:8]1[N:9]=[N:10][S:11][CH:12]=1)[C:5]([OH:7])=O.[NH2:13][CH:14]1[C:29](=[O:30])[N:16]2[C:17]([C:26]([OH:28])=[O:27])=[C:18]([CH2:21][O:22][C:23](=[O:25])[NH2:24])[CH2:19][S:20][C@H:15]12>>[CH3:1][O:2][N:3]=[C:4]([C:8]1[N:9]=[N:10][S:11][CH:12]=1)[C:5]([NH:13][CH:14]1[C:29](=[O:30])[N:16]2[C:17]([C:26]([OH:28])=[O:27])=[C:18]([CH2:21][O:22][C:23](=[O:25])[NH2:24])[CH2:19][S:20][C@H:15]12)=[O:7]

Participants

3

Reactant 2

HCID 127847593-Carbamoyloxymethyl-7-amino-3-cephem-4-carboxylic acidHCID 543473402-Methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetic acid

Product 1

HCID 1317121917-[2-Methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acidYield 45.6%

Procedure

2-Methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetic acid (syn isomer)(0.65 g) and 7-amino-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (0.96 g) were reacted according to similar manners to those of Examples 12 and 15 to give 7-[2-methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer) (0.7 g).

Sources & evidence

ORD record
ord-d333b7d02df84db490619ebeb0134ae3
Source dataset
uspto-grants-1981_04
Patent number
US04263291

Reaction notes

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