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

HRID 1248881Notes

Reaction equation

HRID 1248881 reaction equation
Br[CH2:2][C:3]([NH:5][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:4].[SH:30][C:31]1[S:32][CH:33]=[C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:35]=1>>[C:36]1([C:34]2[N:35]=[C:31]([S:30][CH2:2][C:3]([NH:5][CH:6]3[C:28](=[O:29])[N:8]4[C:9]([C:25]([OH:27])=[O:26])=[C:10]([CH2:13][NH:14][C:15](=[O:24])[C:16]5[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=5[Cl:23])[CH2:11][S:12][C@H:7]34)=[O:4])[S:32][CH:33]=2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

3

Reactant 2

HCID 145023507-Bromoacetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acidHCID 1785278304-phenyl-1,3-thiazole-2-thiol

Product 1

HCID 145023567-(4-Phenyl-1,3-thiazole-2-ylthio)acetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acidYield 62%

Procedure

1.0 g. of 7-bromoacetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acid and 0.39 g. of 2-mercapto-4-phenyl-1,3-thiazole were reacted and worked up according to the method of Example 15. Thus 0.78 g. o(62%) of 7-(4-phenyl-1,3-thiazole-2-ylthio)acetamido-3-(2,6-dichlorobenzoylamino)methylceph-3-em-4-carboxylic acid were obtained.

Sources & evidence

ORD record
ord-6291d096d11446bea1bd34f6ac21e5a5
Source dataset
uspto-grants-1986_12
Patent number
US04626533

Reaction notes

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