(S)-2-(N-methylhexanamido)pent-4-enoic acid → N-((2S)-1-((2S,3R)-4-(3-(allyloxy)-6-phenoxy-2,3-dihydro-1H-inden-1-ylamino)-3-(tert-butyldimethylsilyloxy)-1-phenylbutan-2-ylamino)-1-oxopent-4-en-2-yl)-N-methylhexanamide

Participants

Reaction Steps

Step EW (1): (S)-2-(N-Methylhexanamido)pent-4-enoic acid (420 mg, 1.8 mmol) and (2R,3S)-N1-(3-(allyloxy)-6-phenoxy-2,3-dihydro-1H-inden-1-yl)-2-(tert-butyldimethylsilyloxy)-4-phenylbutane-1,3-diamine (1.0 g, 1.8 mmol, from Preparation BC) were coupled using a procedure analogous to Step CA (1) to afford 900 mg (65% yield) of N-((2S)-1-((2S,3R)-4-(3-(allyloxy)-6-phenoxy-2,3-dihydro-1H-inden-1-ylamino)-3-(tert-butyldimethylsilyloxy)-1-phenylbutan-2-ylamino)-1-oxopent-4-en-2-yl)-N-methylhexanamide. LC-MS (M+H)+=768.65; 1H NMR (300 MHz, CDCl3) δ ppm 0.0 (m, 6H) 0.7-0.9 (m, 12H) 1.0-1.4 (m, 6H) 1.4-1.7 (m, 3H) 1.7-2.3 (m, 4H) 2.4 (s, 3H) 2.5-3.0 (m, 4H) 3.5-3.8 (m, 1H) 4.0-4.4 (m, 4H) 4.7-4.8 (m, 1H) 4.8-5.4 (m, 4H) 5.5-6.1 (m, 2H) 6.8-7.4 (m, 13H).

Provenance & Evidence