Triethylamine → Isohexane ethyl acetate

Participants

Reaction Conditions

Reaction Steps

A 50% solution of 1-propylphosphonic acid cyclic anhydride in DMF (226 mg) was added to a stirred solution of (S)-(−)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (81 mg), (S)-2-amino-3-(4-(phenylsulfonyl)phenyl)propanamide (90 mg) and triethylamine (0.206 mL) in DMF (2 mL) at 0° C. The resulting solution was stirred at 0° C. for 30 min then warmed to room temperature and stirred for a further 30 min. Water (50 mL) and saturated brine (30 mL) were added and the mixture was extracted with ethyl acetate (2×50 mL). The combined organic phases were washed with 1:1 water/saturated brine (2×50 mL), dried over magnesium sulfate and the filtrate was concentrated in vacuo to afford a dark oil contaminated with DMF. This was purified by flash silica chromatography, eluting with 1:2 then 2:1 ethyl acetate/isohexane, then ethyl acetate to give the subtitle compound (125 mg) as a brown oil.

Provenance & Evidence