Sodium Azide → HCID 71182984, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 8 (325 mg, 0.639 mmol) in anhydrous N,N-dimethylformamide (7 mL) was added sodium azide (415 mg, 6.39 mmol). The reaction mixture was heated to 65° C. and stirred overnight. Excess sodium azide was filtered off and the solvent was removed by rotary evaporation. The crude residue was dissolved in ethyl acetate and washed with water three times. The organic layer was dried over sodium sulfate and concentrated followed by flash chromatography in hexanes/ethyl acetate (4:3) to give 10 (206 mg, 71%). 1H NMR (500 MHz, CD3CN) δ 5.62 (1H, s, 4-H), 4.72 (1H, d, J=17, COCH2O), 4.53 (1H, d, J=17, COCH2O), 3.31 (2H, t, J=6.5, CH2N3), 2.55-0.99 (complex, 26H), 1.17 (3H, s, CH3), 0.64 (3H, s, CH3); 13C NMR (125 MHz, CD3CN) δ 204.49, 199.18, 173.04, 171.81, 123.86, 69.81, 59.25, 56.55, 54.21, 51.43, 44.95, 39.12, 38.60, 36.20, 35.94, 34.28, 33.36, 32.96, 32.52, 28.46, 24.79, 23.62, 23.07, 21.46, 17.35, 13.20. ESI-MS m/z [M+Na]+ observed: 478.3, calculated: 478.3.

Provenance & Evidence