Diisopropylethylamine → (1S)-N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-isopropylcyclopent-2-ene-1-carboxamide

Participants

Reaction Steps

HATU (33 g, 88.4 mmol) was added to a cooled (0° C.) mixture of (1S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-isopropylcyclopent-2-ene-1-carboxylic acid (20 g, 80.3 mmol), [2-tert-butoxy-5-(trifluoromethyl)benzyl]amine (24 g, 96.4 mmol), and iPr2EtN (42 mL, 241 mmol) in DMF (400 mL). The resulting mixture was allowed to warm to r.t. and was stirred at r.t. for 18 hr. The reaction mixture was diluted with EtOAc and washed with brine (5×). The organic phase was then dried over sodium sulfate and evaporated to dryness. The dark oily residue was purified by column chromatography on silica gel eluting with hexane:EtOAc (7:3) to yield 46 g of (1S)—N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-isopropylcyclopent-2-ene-1-carboxamide as a yellow oil.

Provenance & Evidence