Triethylamine → HCID 137195807, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 52 (290 mg 0.65 mmol) in dichloromethane (30 mL) were added 4-dimethylaminopyridine (12 mg, 0.065 mmol) and Et3N (0.45 mL), followed by methanesulfonylchloride dropwise (0.121 mL, 1.30 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 40 min under argon then hydrolyzed with water (20 mL). The organic layer was separated and evaporated. The residual oil was diluted in anhydrous DMF (20 mL). To the solution was added sodium azide (410 mg, 6.5 mmol) and the mixture was heated at 120° C. for 2 h under argon. The reaction was cooled to room temperature, diluted with AcOEt and washed with water. The organic layer was evaporated and the residue was then purified by column chromatography on silica gel column eluting with CH2Cl2-MeOH (9:1) to give 55 (200 mg, 65%) as a white solid. IR 2104 cm−1 (N3); 1H NMR (DMSO-d6) δ 1.08-1.12 (m, 6H, 2×CH3), 2.50-2.79 (m, 2H, H-2′, isobutyryl CH), 2.91-3.01 (m, 1H, H-2′), 4.18-4.23 (m, 1H, H-4′), 4.42-4.56 (m, 2H, H-5′, H-5″), 4.83-4.89 (m, 1H, H-3′), 6.21 (t, 1H, J=5.4 Hz, H-1′), 7.45-7.50 (m, 2H benzoyl), 7.62-7.66 (m, 1H benzoyl), 7.85-7.88 (m, 2H benzoyl), 8.20 (s, 1H, H-8), 11.53 (br s, NH), 11.91 (br s, NH).

Provenance & Evidence