HCID 10131699, compound → (2R,3S)-1-((1R,3R)-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-ylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-ol

Participants

Reaction Steps

Step X (3): trans-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-amine from Step X (2) was reacted with benzyl (S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethylcarbamate according to the conditions described in Step V (1). The crude product was purified using silica gel column chromatography to provide 900 mg (69% yield) of a mixture of benzyl (2S,3R)-4-((1S,3S)-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-ylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate and benzyl (2S,3R)-4-((1R,3R)-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-ylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate. LRMS (M+H)+=553.3; 1H NMR (500 MHz, CDCl3) δ ppm 1.87-2.05 (m, 1H) 2.38-2.50 (m, 1H) 2.69-2.92 (m, 3H) 2.96-3.12 (m, 1H) 3.41-3.51 (m, 1H) 3.72-3.91 (m, 4H) 4.01 (t, J=5.49 Hz, 2H) 4.37-4.47 (m, 1H) 4.80 (d, J=9.16 Hz, 1H) 4.92 (dd, J=15.26, 4.58 Hz, 1H) 4.97-5.08 (m, 2H) 5.17 (d, J=10.38 Hz, 1H) 5.23-5.33 (m, 1H) 5.84-5.99 (m, 1H) 6.60-6.68 (m, 1H) 6.74 (d, J=6.41 Hz, 2H) 6.82 (dd, J=8.24, 1.83 Hz, 1H) 6.91 (s, 1H) 7.20-7.38 (m, 7H).

Provenance & Evidence