N-((1,1-Dimethylethoxy)carbonyl)-3-fluoro-L-phenylalanine → HCID 178501456, compound

Participants

Reaction Steps

To a solution of 2.00 gm of BOC-3-F-Phe-OH (7.06 mmol), 2.09 gm of Arg(NO2)-OMe HCl (7.77 mmol), 1.05 gm of hydroxybenzotriazole and 2.58 gm of 4-dimethylaminopyridine in 50 mL of methylene chloride was added 1.5 gm of 1,3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride. After stirring for 15 hours 100 mL more methylene chloride was added to the reaction, and it was washed three times with 100 mL portions of 10% aqueous hydrochloric acid solution, twice with 100 mL of 50% saturated sodium bicarbonate solution, once with 100 mL of saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent removed under reduced pressure to yield 2.96 gm of product. This was dissolved in 100 mL of 10% trifluoroacetic acid in methylene chloride, stirred for 2 hours, and the solvent removed rapidly under reduced pressure. The material was triturated with diethyl ether and dried under high vacuum to yield product.

Provenance & Evidence