Triethylamine → HCID 18663369, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from Step B (500 mg, 1.37 mmol) in 9.6 mL of THF at 0° C. was added triethylamine (1.2 mL, 8.6 mmol), followed by triphosgene (251 mg, 0.847 mmol). The reaction was stirred at 0° C. for one hour, then poured into EtOAc and washed with sat. aq. NaHCO3 and brine. The solution was dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by silica gel chromatography (2.5-5% MeOH/CH2Cl2), then taken up in methanol and injected onto a preparative HPLC column and purified with a mixed gradient of 25%-55% acetonitrile/0.1% TFA; 75%-45% 0.1% aqueous TFA over 50 minutes. After concentration in vacuo, the resultant product was partitioned between dichloromethane and aq. NaHCO3 soln., and the aqueous phase was extracted with CH2Cl2. The organic solution was washed with brine, dried (Na2SO4), filtered, and concentrated to dryness to provide the product free base, which was taken up in CH2Cl2 and treated with excess 1M HCl/ether solution. After concentrated in vacuo, the titled product (57.3 mg) was isolated as a white powder.

Provenance & Evidence