Sodium Azide → (3R,4R,5S)-5-azido-4-(diethoxy-phosphorylamino)-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 104 mg of 18 in 0.50 mL of EtOH and 0.50 mL of DMSO in a 5.0 mL round-bottom flask equipped with a magnetic stirrer, a reflux condenser and an inert gas supply was added 28 mg sodium azide and the reaction mixture was stirred at 85-90° C. for 20 h. The brown reaction mixture was cooled to RT diluted with 1.0 mL of EtOAc and extracted with 1.0 mL of aqueous 1 M NaHCO3. The separated organic phase was dried (Na2SO4), filtered and evaporated at 40° C./120-10 mbar to obtain 40 mg of the crude product as brown crystals. The crude product was dissolved in 0.40 mL methylcyclohexane, stirred for 5 h at RT. The white crystals which formed were filtered and washed with 0.15 mL of methylcyclohexane, dried at 40° C./10 mbar for 2 h to afford 14 mg of 26 as white crystals.

Provenance & Evidence