7-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acid → HCID 131712185, compound

HRID 1703009Notes

Reaction equation

HRID 1703009 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:31](=[O:32])[N:16]2[C:17]([C:28]([OH:30])=[O:29])=[C:18]([CH2:21][S:22][C:23]3[S:24][CH:25]=[N:26][N:27]=3)[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:31](=[O:32])[N:16]2[C:17]([C:28]([OH:30])=[O:29])=[C:18]([CH2:21][S:22][C:23]3[S:24][CH:25]=[N:26][N:27]=3)[CH2:19][S:20][C@H:15]12)=[O:7]

Participants

3

Reactant 2

HCID 128891877-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acidHCID 543473402-Methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetic acid

Product 1

HCID 131712185HCID 131712185, compoundYield 43.7%

Procedure

2-Methoxyimino-2-(1,2,3-thiadiazol-4-yl)-acetic acid (syn isomer) (0.6 g.) and 7-amino-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (1.1 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-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.7 g.), mp 90° to 98° C. (dec.).

Sources & evidence

ORD record
ord-5621e67f505f4889a56dbb859f84c653
Source dataset
uspto-grants-1982_09
Patent number
US04350693

Reaction notes

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