7-[2-(2-Aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid hydrochloride → 7-[2-(2-Aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid
Reaction equation
Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=[N:31][O:32][CH2:33][CH2:34][OH:35])[C:9]([NH:11][CH:12]2[C:29](=[O:30])[N:14]3[C:15]([C:26]([OH:28])=[O:27])=[C:16]([CH2:19][S:20][C:21]4[S:22][CH:23]=[N:24][N:25]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[N:7]=1>O>[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=[N:31][O:32][CH2:33][CH2:34][OH:35])[C:9]([NH:11][CH:12]2[C:29](=[O:30])[N:14]3[C:15]([C:26]([OH:28])=[O:27])=[C:16]([CH2:19][S:20][C:21]4[S:22][CH:23]=[N:24][N:25]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[N:7]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 7-[2-(2-aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid hydrochloride (syn isomer, 10.5 g.) in water (300 ml.) was adjusted to pH 4.0 and subjected to column chromatography on nonionic adsorption resin "Diaion HP-20" (trademark, manufactured by Mitsubishi Chemical Industries Ltd.). After washing the column with water (200 ml.), the object compound was eluted with 20% isopropyl alcohol. The eluate was lyophilized to give 7-[2-(2-aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 7.2 g.).
Workup
- washAfter washing the column with water (200 ml.)
- washthe object compound was eluted with 20% isopropyl alcohol
Sources & evidence
- ORD record
- ord-0830735ac0504171a052f00fb287ba97
- Source dataset
- uspto-grants-1987_10
- Patent number
- US04698337
Reaction notes
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