Triethylamine → HCID 86605389, compound

Participants

Reaction Steps

A solution of methyl (2S)-4-methyl-2-{[(R)-[4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)phenyl](phenyl)methyl]oxy}pentanoate from example 36 step 4 (100 mg, 0.25 mmol), THF (1.5 mL), methanol (0.5 mL) and IN KOH (0.5 mL) was heated at 70° C. for 45 min. The mixture was concentrated and then 2 times with toluene to dry. To the residue was added DMF (1.5 mL), aminoacetonitrile hydrochloride (23 mg, 0.25 mmol), HATU coupling reagent (95 mg, 0.25 mmol) and triethylamine (75 mg, 0.75 mmol). The reagents were stirred at r.t. for 2 h, then added to dilute brine (5 mL) and extracted with 1:1 THF/ethyl acetate (25 mL). The organic layer was washed with brine (2×10 mL), dried (Na2SO4), filtered, concentrated and the residue purified by chromatography on silica gel using 10% methanol in dichloromethane to obtain the title compound as a white solid.

Provenance & Evidence