Trifluoroacetic acid → HCID 131720345, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-Boc-L-leucine-L-leucine N,O-dimethylhydroxylamide (923 mg) and trifluoroacetic acid (10 mL) in methylene chloride (20 mL) was stirred at 0° C. for 3 hours. The solvent was evaporated under reduced pressure and the residue was dried under vacuum. A portion of this product (488 mg) was transferred to another flask and was combined with Z-L-leucine (451 mg), 1-hydroxybenzotriazole monohydrate (276 mg), N-methylmorpholine (0.22 mL), and DMF (15 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (357 mg) was then added at 0° C. The mixture was stirred at 0° C. for 2 h, then at room temperature for 42 h. The reaction was quenched with water (50 mL) and the mixture was extracted with EtOAc (3×60 mL). The combined organic layers were washed with aqueous 10% HCl, saturated NaHCO3, and brine, then dried over anhydrous MgSO4, filtered, and evaporated to afford the product as a white solid. This was further purified by silica gel chromatography (hexane/acetone 80:20, 70:30) to give the title compound (546 mg) as a white solid.

Provenance & Evidence