Triethylamine → HCID 22241627, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the product from Step B (0.12 g, 0.37 mmol) and methanesulfonyl chloride (0.04 ml, 0.48 mmol) in CH2Cl2 (5 ml) and under nitrogen was cooled to 0° C. and triethylamine (0.07 ml, 0.48 mmol) was added. The resulting mixture was stirred at 0° C. for 10 min followed by the addition of a saturated aqueous solution of NH4Cl (20 ml) and ethyl acetate (20 ml). The aqueous layer was separated and extracted with ethyl acetate (2×5 ml). The combined extracts were washed with a saturated aqueous solution of NaCl (2×15 ml), dried (MgSO4), and evaporated to a residue which was dissolved in DMF (3 ml). Sodium azide (0.08 g, 1.2 mmol) was added and the mixture was stirred at 70° C. for 18 h. After cooling, water (20 ml) and ether (20 ml) were added and the aqueous layer was separated and further extracted with ether (3×20 ml). The combined extracts were washed with a saturated aqueous solution of NaCl (3×15 ml), dried (MgSO4), and evaporated to a residue that was purified by chromatography (silica, 10% ethyl acetate in hexane) to give a yellow oil (0.12 g). MS(ES) m/z 350 (M+H)+.

Provenance & Evidence