HCID 15956062, compound → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl) (isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate

Participants

Reaction Steps

A solution of 8.00 g (11.7 mmol) of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-[4-(benzyloxy)benzyl]-2-hydroxypropylcarbamate in 200 mL of THF was subjected to hydrogenation at 50 psi in the presence of 8.0 g of 10% palladium on carbon (Degussa type). After 18 hours the reaction vessel was purged with nitrogen, catalyst removed by filtration through celite, and the filtrate concentrated at reduced pressure to a volume of 30 mL. The solution was rapidly stirred with addition of 30 mL of EtOAc followed by 250 mL of hexane. A white suspension resulted which was stirred at RT for 1 hour. The solid was collected by vacuum filtration and dried in vacuo to afford 6.83 g (98%) of (the desired compound as a white powder. 1H NMR (DMSO-d6): 9.00 (s, 1H), 7.25 (d, 1H), 7.17 (s, 1H), 7.12 (d, 1H), 7.01 (d, 1H), 6.92 (d, 2H), 6.52 (d, 2H), 6.12 (S, 2H), 5.46 (d, 1H), 4.93 (d, 1H), 4.80 (q, 1H), 3.80 (dd, 1H), 3.70 (t, 1H), 3.52 (m, 3H), 3.40 (m, 1H), 3.25 (m, 1H), 3.01-2.62 (m, 5H), 2.28 (t, 1H), 1.89 (m, 1H), 1.38 (m, 1H), 1.22 (m, 1H), 0.80 (d, 3H), 0.72 (d, 3H). MS(ESI): 593(M+H).

Provenance & Evidence