Phosphorus pentachloride → HCID 20294431, compound
Reaction equation
[CH2:1]([S:3]([O:6][C:7]1[CH:11]=[C:10]([CH2:12][C:13]([OH:15])=O)[O:9][N:8]=1)(=[O:5])=[O:4])[CH3:2].P(Cl)(Cl)(Cl)(Cl)[Cl:17]>C(Cl)Cl>[CH2:1]([S:3]([O:6][C:7]1[CH:11]=[C:10]([CH2:12][C:13]([Cl:17])=[O:15])[O:9][N:8]=1)(=[O:5])=[O:4])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
650 mg of (3-ethanesulphonyloxyisoxazol-5-yl)acetic acid were dissolved in 7 ml of methylene chloride, 577 mg of phosphorus pentachloride were added thereto, and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off and the residual (3-ethanesulphonyloxyisoxazol-5-yl)acetyl chloride thus obtained was dissolved in 5 ml of methylene chloride. This solution was added to a solution of 300 mg of benzhydryl 7β-amino-7α-methoxy-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylate and 207 mg of N,N-diethylaniline in 4 ml of methylene chloride. The reaction mixture was stirred in an ice bath for 1 hour and then the solvent was distilled off. The residue was dissolved in ethyl acetate and the solution was washed with, in turn, dilute aqueous potassium bisulphate, aqueous sodium chloride, aqueous sodium hydrogen carbonate and aqueous sodium chloride, and then dried over anhydrous magnesium sulphate. The solvent was distilled off and the residue was adsorbed on a silica gel preparative thin layer chromatograph and developed with a 1:1 by volume mixture of benzene and ethyl acetate. The portion having an Rf value of 0.63 was extracted with ethyl acetate. The solvent was distilled under reduced pressure from the extract to give 422 mg (100%) of the benzhydryl ester of the desired Compound No. 15.
Workup
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-0151efa9ffc04b358589e9cef5bd9585
- Source dataset
- uspto-grants-1981_01
- Patent number
- US04247548
Reaction notes
Loading…