Nitrogen → HCID 89183088, compound

Participants

Reaction Steps

tert-butyl ((3S)-1-(4-azido-5-isothiazolyl)-3-piperidinyl) carbamate. A 25 mL, one neck round bottom flask was charged with tert-butyl ((3S)-1-(4-amino-5-isothiazolyl)-3-piperidinyl)carbamate (537 mg, 1.80 mmol), acetone (7 mL), water (7 mL) and a stirbar. The flask was immersed into a ice-water bath and stirred for 15 min. The solution was treated with 8 M H2SO4 (0.90 mL, 7.19 mmol), and stirred for 5 min. The homogenous solution was treated with NaNO2 (163 mg, 2.36 mmol) and stirred for 10 min. NaN3 (351 mg, 5.40 mmol) was added. The reaction was stirred cold for 30 min. The slurry was N2-pressure filtered cold through a 10 mL Bohdan glass frit fitted with a 0.22 μm PTFE, 25 mm syringe filter unit (Millipore, SLFG025NK). The filtrate was slowly added to a ice-cold solution of Na2CO3 (1.14 g, 10.79 mmol) in H2O (10 mL). The solids were washed with H2O (3×5 mL), and the washes were added to the Na2CO3 solution. The solids were dried in a vacuum oven (45° C., <1 mm Hg) for 20 min. The solids were dissolved in CHCl3, and treated with MgSO4. The resulting slurry was N2-pressure filtered through a 10 mL Bohdan glass frit fitted with a 0.22 μm PTFE, 25 mm syringe filter unit (Millipore, SLFG025NK). The solvent was removed in vacuo to afford tert-butyl ((3S)-1-(4-azido-5-isothiazolyl)-3-piperidinyl)carbamate (213 mg, 0.66 mmol, 37% yield). The material was used directly.

Provenance & Evidence