Acetic Acid → HCID 178496735, compound

Participants

Reaction Steps

To a solution of Boc-Thr(Me)-OH (113 mg, 0.48 mmol) in N,N-dimethylformamide (3.0 mL) was added HATU (225 mg, 0.592 mmol). The mixture was stirred for 30 minutes and then 4-cyclopentylbenzene-1,2-diamine (Compound 84, 118 mg, 0.669 mmol) was added. After stirring for 2 days, the solution was diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulphate, filtered, and concentrated in vacuo. To the resulting residue was added acetic acid (3 mL, 50 mmol) and the mixture allowed to stir for 2 days. The reaction mixture was then concentrated in vacuo and purified by silica gel column chromatography eluting with 0-100% ethyl acetate in hexanes. The resulting brown oil was dissolved in methylene chloride (5 mL) and treated with trifluoroacetic acid (0.5 mL, 6 mmol). After stirring for 3 hours, the reaction mixture was concentrated in vacuo, redissolved in methylene chloride, and washed with saturated aqueous sodium hydrogen carbonate solution.

Provenance & Evidence