(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane → tert-butyl (2S,3R)-4-((1S,3R)-3-(allyloxy)-6-methyl-2,3-dihydro-1H-inden-1-ylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate

Participants

Reaction Steps

Step BK (3): The product from Step BK (2) was reacted with tert-butyl (S)-1-((S)-oxiran-2-yl)-2-phenylethylcarbamate (271 mg, 1.03 mmol) following a procedure analogous to Step AW (1) to afford 415 mg (86% yield) of tert-butyl (2S,3R)-4-((1S,3R)-3-(allyloxy)-6-methyl-2,3-dihydro-1H-inden-1-ylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate. LC-MS (M+H)+=467.29; 1H NMR (500 MHz, CDCl3) δ ppm 7.39-7.16 (m, 7H) 5.93-5.87 (m, 1H) 5.33-4.60 (m, 8H) 4.08 (d, 2H) 3.94 (m, 1H) 3.62 (m, 1H) 3.46 (d, 1H) 3.10-3.06 (m, 2H) 3.6 (m, 1H) 2.59-2.54 (m, 2H) 2.37 (s, 3H) 1.25 (s, 9H).

Provenance & Evidence