Water → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-4,5,22,28-tetramethyl-17-(trifluoromethoxy)-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate

Participants

Reaction Steps

A solution of (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-7,8-dimethyl-2-(2′-((S)-pent-4-en-2-yloxy)-5′-(trifluoromethoxy)-[1,1′-biphenyl]-3-yl)imidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate (0.20 g, 0.262 mmol, 1 equiv) and TsOH monohydrate (50 mg, 0.262 mmol, 1 equiv) in DCE (100 mL) was heated to 80° C. The Hoveyda Grubbs 2nd generation catalyst (16 mg, 0.026 mmol, 0.1 equiv) was added. The pale green brown solution was stirred for 3 h. Upon cooling to ambient temperature, the reaction was washed with saturated aqueous NaHCO3, dried (Na2SO4), and concentrated in vacuo. The crude product was taken up in 20:1 DCE:water (2.8 mL) and tetrabutylammonium borohydride (135 mg, 0.524 mmol, 2 equiv) was added. After 1 h, the reaction mixture was diluted with DCM, washed with water, dried (Na2SO4), and concentrated in vacuo. The crude product was purified by silica gel flash column chromatography (0-100% EtOAc [2% TEA]/hexane) to provide the product (74 mg, 38%) as a tan foam. LCMS (ESI, M+1): 738.80.

Provenance & Evidence