Diisopropylethylamine → HCID 86658400, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of (2S)-N-((1R)-2-amino-1-(4-(2-methylpentyloxy)phenyl)ethyl)-2-phenylpropanamide (200 mg, 0.543 mmol), prepared according to the procedure described in example 5, in dichloromethane (4 mL) was cooled to 0° C. To this solution, Boc-L-isoleucine (188 mg, 0.814 mmol), N,N-diisopropylethylamine (0.569 mL, 3.26 mmol) and HATU (310 mg, 0.814 mmol) were added. The ice-water bath was removed and reaction mixture was stirred at room temperature for 3 h. The mixture was transferred to a separatory funnel containing saturated aqueous NaHCO3 solution (60 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (30→40% ethyl acetate in hexanes) to afford t-butyl (2S,3S)-3-methyl-1-((2R)-2-(4-(2-methylpentyloxy)phenyl)-2-((S)-2-phenylpropanamido)ethylamino)-1-oxopentan-2-ylcarbamate (190 mg, 60% yield) as a colorless solid: LRMS (ESI) m/e 582.4 [(M+H)+, calcd for C34H52N3O5 582.4].

Provenance & Evidence