7-Bromoacetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acid → 7-(1,2,3,4-Thiatriazole-5-ylthio)-acetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acid

HRID 1248883Notes

Reaction equation

HRID 1248883 reaction equation
BrCC(N[CH:6]1[C:28](=[O:29])[N:8]2[C:9]([C:25]([OH:27])=[O:26])=[C:10]([CH2:13][NH:14][C:15](=[O:24])[C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:23])[CH2:11][S:12][C@H:7]12)=O.[SH:30][C:31]1[S:35][N:34]=[N:33][N:32]=1>>[S:35]1[C:31]([S:30][CH:6]2[C:28](=[O:29])[N:8]3[C:9]([C:25]([OH:27])=[O:26])=[C:10]([CH2:13][NH:14][C:15](=[O:24])[C:16]4[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=4[Cl:23])[CH:11]([NH:14][C:15](=[O:24])[CH3:16])[S:12][C@H:7]23)=[N:32][N:33]=[N:34]1

Participants

3

Reactant 2

HCID 145023507-Bromoacetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acidHCID 178527995HCID 178527995, compound

Product 1

HCID 1317149867-(1,2,3,4-Thiatriazole-5-ylthio)-acetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acidYield 65%

Procedure

1.0 g. of 7-bromoacetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acid and 0.24 g. of 5-mercapto-1,2,3,4-thiatriazole were reacted and worked up according to the method of Example 15. Thus 0.73 g. (65%) of 7-(1,2,3,4-thiatriazole-5-ylthio)-acetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acid were obtained.

Sources & evidence

ORD record
ord-556aab5d7c9f4d5f90e2b8f00f5c9e27
Source dataset
uspto-grants-1986_12
Patent number
US04626533

Reaction notes

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