Acetic Acid → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][CH3:27])/[C:8]([NH:10][C@@H:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH2:18]O)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.P(OCC)(OCC)OCC.C(O)(=O)C>C(#N)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][CH3:27])/[C:8]([NH:10][C@@H:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([O-:22])=[O:21])=[C:15]([CH2:18][N+:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22.5 °C
Procedure
In 2 ml of acetonitrile was suspended 103 mg of 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-hydroxymethyl-3-cephem-4 -carboxylic acid. To the suspension were added in sequence 0.10 ml of pyridine, 0.21 ml of triethyl phosphite and 0.2 ml of acetic acid. The mixture was stirred at 20 to 25° C. for 8 hours, followed by concentration under reduced pressure. To the concentrated solution was added 10 ml of tetrahydrofuran, then precipitating powdery product was collected by filtration, followed by concentration under reduced pressure to give 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-(1 -pyridinio)methyl-3-cephem-4-carboxylate.
Workup
- concentrationfollowed by concentration under reduced pressure
- additionTo the concentrated solution was added 10 ml of tetrahydrofuran
- filtrationprecipitating powdery product was collected by filtration
- concentrationfollowed by concentration under reduced pressure
Sources & evidence
- ORD record
- ord-6b03fd7f91794cc78699a3531a070d84
- Source dataset
- uspto-grants-1990_12
- Patent number
- US04980464
Reaction notes
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