Hydrochloric Acid → 7-[2-(2-aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid dihydrochloride
Reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:33][O:34][CH2:35][CH2:36][NH2:37])[C:10]([NH:12][CH:13]2[C:31](=[O:32])[N:15]3[C:16]([C:28]([OH:30])=[O:29])=[C:17]([CH2:20][S:21][C:22]4[N:26]([CH3:27])[N:25]=[N:24][N:23]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.[ClH:38]>CO>[ClH:38].[ClH:38].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:33][O:34][CH2:35][CH2:36][NH2:37])[C:10]([NH:12][CH:13]2[C:31](=[O:32])[N:15]3[C:16]([C:28]([OH:30])=[O:29])=[C:17]([CH2:20][S:21][C:22]4[N:26]([CH3:27])[N:25]=[N:24][N:23]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 0.30 g.), conc. hydrochloric acid (0.14 g.) and methanol (3.5 ml.) was stirred at room temperature for 7 hours. After concentrating the resultant solution in vacuo, the residue was pulverized with a mixture of diisopropyl ether (10 ml.) and methanol (10 ml.). The precipitates were collected by filtration to give 7-[2-(2-aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid dihydrochloride (syn isomer, 0.21 g.).
Workup
- concentrationAfter concentrating the resultant solution in vacuo
- additionthe residue was pulverized with a mixture of diisopropyl ether (10 ml.) and methanol (10 ml.)
- filtrationThe precipitates were collected by filtration
Sources & evidence
- ORD record
- ord-47b26cac31104fc78e79aa2f1057ee57
- Source dataset
- uspto-grants-1987_10
- Patent number
- US04698337
Reaction notes
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