Triethylamine → HCID 86746599, compound

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Reaction Conditions

Reaction Steps

The above-described compound 26, in the amount produced, is dissolved in 50 ml of acetonitrile, and the solution is cooled to 0° C. 2.37 g (12 mmol) of tosyl azide are added to the cooled solution with stirring, and 2.5 g (25 mmol) of triethylamine are subsequently added dropwise at such a rate that the temperature does not exceed 5° C. The mixture is stirred at this temperature for 60 minutes, and subsequently warmed to room temperature. After 2 hours, tosyl azide is no longer detectable in the mixture by thin-layer chromatography (silica gel, dichloromethane as eluent). 1.70 g (7.5 mmol) of 4-carboxyphenylsulfonyl azide are added to the mixture at 0° C., and the mixture is stirred for 30 minutes. After a further 2 hours at room temperature, the solvent is removed by distillation in vacuo. The residue is taken up in dichloromethane, and the solution is washed three times with 200 ml of 10% aqueous potassium hydroxide solution in each case. The mixture is subsequently washed with water until neutral, and the organic phase is dried using sodium sulfate. Evaporation leaves a red oil, which is substantially freed from solvent residues by applying a high vacuum. Column chromatography on silica gel using dichloromethane/ethyl acetate as eluent gives 5.4 g of colorless α-diazo-β-keto ester/sulfonate 27, which has the following composition.

Provenance & Evidence