Thionyl Chloride → 2-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetyl chloride
Reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH3:15])[C:10](O)=[O:11])[N:8]=1)=[O:2].S(Cl)([Cl:18])=O>CN(C)C=O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH3:15])[C:10]([Cl:18])=[O:11])[N:8]=1)=[O:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
N,N-Dimethylformamide (3 drops) was added to a suspension of 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 23 g.) in thionyl chloride (230 ml) and stirred at 60° C. for 5 minutes. After concentrating the solution in vacuo, benzene was added to the residue. The precipitates were collected by filtration, washed with benzene (30 ml.) three times and diethyl ether in turn to give 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetyl chloride (anti isomer, 18 g.). On the other hand, trimethylsilylacetamide (46 g.) was added to a suspension of 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (16.8 g.) in methylene chloride (168 ml.), and stirred at 40° C. for an hour. To the suspension was gradually added 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetyl chloride (anti isomer, 13.6 g.) at -5° to 0° C., and stirred at the same temperature for an hour. Water (150 ml.) was added to the resultant solution and stirred for 15 minutes. The recipitates were collected by filtration, washed with water and dried over phosphorus pentoxide under reduced pressure to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (anti isomer, 25.7 g.).
Workup
- concentrationAfter concentrating the solution in vacuo, benzene
- additionwas added to the residue
- filtrationThe precipitates were collected by filtration
- washwashed with benzene (30 ml.) three times and diethyl ether in turn
Sources & evidence
- ORD record
- ord-1354433dbda140f7b91775f6cdfa2ffe
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04427674
Reaction notes
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