Triethylamine → HCID 86609879, compound

Participants

Reaction Steps

4.32 g of methanesulphonyl chloride (MW: 114.55, 37.82 mmol) were added at 10° C., with stirring, to a mixture of 10 g of (5R)-3-(4-benzyloxy-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one (MW: 317.32, 31.51 mmol) and 4.78 g of triethylamine (MW: 101.19, 47.26 mmol) in 300 ml of dichloromethane. The reaction mixture was stirred at RT for 1 h and the course of the reaction was monitored by TLC (ethyl acetate/hexane 1/1). The reaction was quenched with 100 ml of water and the organic phase was washed with 100 ml of saturated sodium chloride solution. The organic phase was dried over magnesium sulphate and filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in 100 ml of dimethylformamide and 5.12 g of sodium azide (MW: 65.01, 78.7 mmol) and a catalytic amount of tetrabutylammonium iodide was added. The suspension was stirred overnight at 90° C. The course of the reaction was monitored by HPLC. The dimethylformamide was removed under reduced pressure using a rotary evaporator, the residue was dissolved in 200 ml of dichloromethane and the organic phase was washed in succession with 100 ml of water and 100 ml of saturated sodium chloride solution. The dichloromethane solution was dried over magnesium sulphate and filtered, and the filtrate was concentrated under reduced pressure. The residue was crystallised from 150 ml of ethyl acetate/hexane 1/1. Yield: 10.4 g, 97%. MS: 343.1 (M+H)+. Method: ESI+.

Provenance & Evidence