Sodium Azide → Tert-butyl 2-hydroxy-3-[(2-pyridinylsulfonyl)amino]propylcarbamate

Participants

Reaction Conditions

Reaction Steps

First, 21 g (121 mmol) of tert-butyl 2-oxiranylmethylcarbamate was dissolved in 90 mL of dimethylformamide and 11.8 g (182 mmol) of sodium azide was added. The reaction mixture was stirred at 65° C. overnight. The dimethylformamide was removed and ether was added. The ether layer was washed with brine (3×), dried over anhydrous magnesium sulfate, and concentrated. The residue was dissolved in 50 mL of methanol and hydrogenated with 2 g of 10% palladium on carbon under 45 psi of hydrogen gas at room temperature overnight. The catalyst was removed by filtration and the filtrate was concentrated. The residue was dissolved in 30 mL of dichloromethane, and 17.7 mL (17.7 mmol) of 1M 2-pyridinylsulfonyl chloride in dichloromethane and 3.8 mL (21.8 mmol) of N,N-diisopropylethylamine were added. The reaction mixture was stirred at room temperature overnight. After removal of solvent, purification by column chromatography with hexane:ethyl acetate (1:2) as eluant gave 350 mg (0.9%) of tert-butyl 2-hydroxy-3-[(2-pyridinylsulfonyl)amino]propylcarbamate. 1H-NMR (300 MHz CDCl3): δ 8.72 (d, J=6 Hz, 1H), 8.05 (d, J=8 Hz, 1H), 7.97 (t, J=8 Hz, 1H), 7.55 (m, 1H), 6.10 (br s, 1H), 5.11 (br s, 1H), 4.33 (d, J=5 Hz, 1H), 3.81 (m, 1H), 3.36–3.20 (m, 4H), 1.44 (s, 9H). ES-LCMS: 332 (M+H).

Provenance & Evidence