Sodium Bicarbonate → 3-Carbamoyloxymethyl-7-(2-aminothiazol-4-yl)acetamido-3-cephem-4-carboxylic acid
Reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].C(=O)(O)[O-].[Na+].[C:10]([O:13][CH2:14][C:15]1[CH2:16][S:17][C@@H:18]2[CH:25]([NH:26][C:27](=[O:33])[CH2:28][C:29](=O)[CH2:30]Br)[C:24](=[O:34])[N:19]2[C:20]=1[C:21]([OH:23])=[O:22])(=[O:12])[NH2:11]>O1CCCC1.O>[C:10]([O:13][CH2:14][C:15]1[CH2:16][S:17][C@@H:18]2[CH:25]([NH:26][C:27](=[O:33])[CH2:28][C:29]3[N:1]=[C:2]([NH2:4])[S:3][CH:30]=3)[C:24](=[O:34])[N:19]2[C:20]=1[C:21]([OH:23])=[O:22])(=[O:12])[NH2:11]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of thiourea (0.103 g.) and sodium bicarbonate (0.11 g.) in a mixture of tetrahydrofuran (1.3 ml.) and water (1.3 ml.) was gradually added 3-carbamoyloxymethyl-7-(3-oxo-4-bromobutyramido)-3-cephem-4-carboxylic acid (0.55 g.) with stirring at room temperature, and then the resulting solution was stirred for 40 minutes at room temperature. After the reaction, the precipitated crystals were collected by filtration with suction, washed with water, tetrahydrofuran and water in turn, and then dried over phosphorus pentoxide to give 3-carbamoyloxymethyl-7-(2-aminothiazol-4-yl)acetamido-3-cephem-4-carboxylic acid (0.48 g.).
Workup
- stirringthe resulting solution was stirred for 40 minutes at room temperature
- customAfter the reaction
- filtrationthe precipitated crystals were collected by filtration with suction
- washwashed with water, tetrahydrofuran and water in turn
- dry with materialdried over phosphorus pentoxide
Sources & evidence
- ORD record
- ord-02766dc8baee4c4db7909a7b4e1fc0fb
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04254260
Reaction notes
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