Hydrochloric Acid → HCID 22969540, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 15.0 g (40.4 mmol) of 5-amino-1-(4-fluorophenyl)-4-[3-{2(S),3-dihydroxypropoxy}benzoyl]pyrazole in 150 ml THF was added 17 ml (168 mmol) of triethylamine. The mixture was cooled to −5° C. and 18 ml of phosgene (20% in toluene) was added over a 30 minute period keeping the reaction temperature below 0° C. Once addition was complete, the reaction was stirred for an additional hour at 0° C. Then, 20 ml of distilled water was added along with 5% HCl until the pH of the solution was 5 to 6. After 30 minutes, ethyl acetate was added and the organic layer was separated, washed with brine, and dried over MgSO4. Filtration and concentration in vacuo gave a yellow oil which was purified by flash column chromatography using 1:1-1:2 hexanes/ethyl acetate as eluent. The desired carbonate precipitated upon concentrating the column fractions to give 7.38 g of desired product.

Provenance & Evidence