Acetyl chloride → 3-Acetyl-3'-azido-5'-O-(3-chlorobenzoyl)-3'-deoxythymidine

Participants

Reaction Steps

To a mixture of 3'-azido-5'-O-(4-chlorobenzoyl)-3'-deoxythymidine (0.3 g, 0.74 mMol) and silver cyanide (0.4 g, 3.0 mMol) in 20 mL of benzene, excess acetyl chloride (2.6 g, 33 mMol) was added in several portions. The mixture was stirred at room temperature until the starting material disappeared (4 hours) as established by TLC CHCl3 /MeOH 20:1 (v/v). The reaction was filtered and the filtrate evaporated under reduced pressure to dryness. The resulting oily residue was chromatographed on silica gel eluted with chloroform/hexane 1:1 (v/v) followed by chloroform to give 0.21 g (64%) of the desired product as an oil.

Provenance & Evidence