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

HRID 1248882Notes

Reaction equation

HRID 1248882 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.[CH3:30][N:31]1[CH:35]=[CH:34][N:33]=[C:32]1[SH:36]>>[CH3:30][N:31]1[CH:35]=[CH:34][N:33]=[C:32]1[S:36][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:17]([Cl:23])=[CH:18][CH:19]=[CH:20][C:21]=3[Cl:22])[CH:11]([NH:14][C:15](=[O:24])[CH3:16])[S:12][C@H:7]12

Participants

3

Reactant 2

HCID 145023507-Bromoacetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acidHCID 178480602HCID 178480602, compound

Product 1

HCID 1317149857-(1-Methylimidazole-2-ylthio)-acetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acidYield 60%

Procedure

1.0 g. of 7-bromoacetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acid and 0.23 g. of 1-methyl-2-mercapto-imidazole were reacted and worked up according to Example 15. Thus 0.67 g. (60%) of 7-(1-methylimidazole-2-ylthio)-acetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acid were obtained.

Sources & evidence

ORD record
ord-bac69fff52db41bfaf2b14340ad1ff95
Source dataset
uspto-grants-1986_12
Patent number
US04626533

Reaction notes

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