Oxalyl chloride → HCID 20294440, compound

HRID 1390045Notes

Reaction equation

HRID 1390045 reaction equation
[C:1]([O:9][C:10]1[CH:14]=[C:13]([CH2:15][C:16]([O-:18])=O)[O:12][N:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].C(Cl)(=O)C([Cl:23])=O>C(Cl)Cl.CN(C)C=O>[C:1]([O:9][C:10]1[CH:14]=[C:13]([CH2:15][C:16]([Cl:23])=[O:18])[O:12][N:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 86737459HCID 86737459, compound

Product 1

HCID 20294440HCID 20294440, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

0.59 g of sodium (3-benzoyloxyisoxazol-5-yl)acetate was suspended in 5 ml of methylene chloride, and 0.37 ml of oxalyl chloride were then added, with ice-cooling. After adding one drop of N,N-dimethylformamide, the mixture was stirred for 30 minutes. The solvent was then distilled off under reduced pressure to give (3-benzoyloxyisoxazol-5-yl)acetyl chloride, which was then dissolved in 5 ml of methylene chloride. This solution was added dropwise to a solution of 685 mg of benzhydryl 3-acetoxymethyl-7β-amino-7α-methoxy-3-cephem-4-carboxylate and 325 mg of N,N-diethylaniline in 5 ml of methylene chloride, maintaining the internal temperature at about -10° C. After stirring the mixture at a temperature between -10° C. and -5° C. for 45 minutes, the reaction mixture was evaporated to dryness under reduced pressure and the residue was adsorbed on a silica gel preparative thin layer chromatograph and developed by a 2:1 by volume mixture of benzene and ethyl acetate. The portion having an Rf value of 0.54 was extracted to give 660 mg (64.7%) of the benzhydryl ester of the desired Compound No. 4.

Workup

  1. temperaturecooling
  2. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-e442238b0b4745a18af6ab2af849d98d
Source dataset
uspto-grants-1981_01
Patent number
US04247548

Reaction notes

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