HCID 86593819, compound → HCID 69736214, compound

Participants

Reaction Steps

To a round bottom flask containing Phosphoric acid dibenzyl ester 4-(S),5-(S)-bis-benzyloxy-6-(R)-benzyloxymethyl-2-(R)-[3-(S)-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indol-1-yl]-tetrahydro-pyran-3-(R)-yl ester (3-(S)-IX) (0.117 g, 0.11 mmol) was added ethyl acetate (1 mL). Platinum oxide (0.013 g, 0.06 mmol) was added to the reaction mixture which was then placed under a hydrogen atmosphere. The reaction was allowed to stir at room temperature overnight. The crude reaction mixture was purified via reverse phase column chromatography (C18, 1:1 water:acetonitrile). The title product was obtained as a white solid (0.045 g, 68%). 1H NMR (MeOH-D4, 400 MHz): δ 7.72 (d, 1H, J=1.8 Hz), 7.5 (s, 1H), 7.38 (dd, 1H, J=6.2 Hz, 2.6 Hz), 7.29 (dd, 1H, J=21.7 Hz, 7.7 Hz), 6.93 (dd, 1H, J=7.7 Hz, 1.1 Hz), 5.61 (d, 1H, J=9.4 Hz), 3.97 (d, 1H, J=11.9 Hz), 3.77 (m, 2H), 3.57 (s, 3H); 19F NMR (MeOH-D4, 376 MHz): δ−64.5, −163.3; 31P NMR (MeOH-D4, 161 MHz): δ 1.54; LRMS: 599 [M−H]−.

Provenance & Evidence