Triethylamine → HCID 25029410, compound

Participants

Reaction Conditions

Reaction Steps

(R)-3-Benzyloxy-2-[4-(4-bromo-phenyl)-thiazol-2-ylamino]-propan-1-ol (110 mg, 0.26 mmol), prepared in the previous step, was dissolved in methylene chloride (10 mL), cooled to 0° C. and triethylamine (0.36 mL, 2.6 mmol) was added followed by triphosgene (0.19 g, 0.65 mmol). The mixture was stirred for 3 h, diluted with methylene chloride and washed with saturated NaHCO3, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (10% acetone in hexane) afforded the title compound (35 mg, 30%). HRMS: calcd for C20H17BrN2O3S+H+, 445.02160; found (ESI, [M+H]+), 445.0201; Analytical HPLC: purity 100% at 210-370 nm, 11.1 min; 93.8% at 238 nm, 11.1 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Provenance & Evidence