HCID 10131699, compound → (2R,3S)-1-((1S,3R)-3-(allyloxy)cyclopentylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-ol

Participants

Reaction Steps

Step Y (3): Racemic cis-3-(allyloxy)cyclopentanamine from step Y (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). Purification by silica gel column chromatography provided 726 mg (51% yield) of a mixture of benzyl (2S,3R)-4-((1R,3S)-3-(allyloxy)cyclopentylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate and benzyl (2S,3R)-4-((1S,3R)-3-(allyloxy)cyclopentylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate. LC-MS (M+H)+=475.3; 1H NMR (500 MHz, CDCl3) δ ppm 1.61-1.92 (m, 3H) 1.93-2.30 (m, 3H) 2.72 (dd, J=13.89, 10.83 Hz, 1H) 3.00 (d, J=9.16 Hz, 1H) 3.18 (t, J=14.34 Hz, 1H) 3.31-3.48 (m, 1H) 3.55-4.18 (m, 5H) 4.39 (dd, J=36.01, 4.88 Hz, 1H) 4.91-5.07 (m, 2H) 5.10-5.31 (m, 2H) 5.43 (dd, J=15.87, 8.55 Hz, 1H) 5.77-5.94 (m, 1H) 6.55-6.81 (m, 3H) 7.00-7.51 (m, 7H).

Provenance & Evidence