Triethylamine → HCID 50923930, compound

Participants

Reaction Steps

To a (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetoxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid (0.4 g, 0.803 mmol) in DCM (1 ml) 2M solution of (COCl)2 in DCM (4 ml, 8.03 mmol) was added at about 0° C. and the reaction mixture was stirred at room temperature for about 3 hours. After completion of the reaction (monitored by TLC) the solvent was evaporated under nitrogen atmosphere and dissolved in DCM (4 ml), which was added to a solution of ((1R,3S)-3-amino-2,2-dimethylcyclobutyl)(morpholino)methanone (Intermediate 11, 0.306 g, 1.45 mmol) in DCM (5 ml) and Et3N (0.22 ml, 1.61 mmol) at about 0° C. and allowed to stir at room temperature for about 16 hours. After completion of the reaction (monitored by TLC) the reaction mixture was diluted with DCM and washed with water, 1N HCl, water brine and dried with Na2SO4, the solvent was evaporated and purified by silica gel column (100-200 mesh, elution 10% EtOAc in hexane) to afford the title compound as an off white solid. Wt: 0.380 g: Yield: 68.4%; 1H NMR (300 MHz, CDCl3): δ 5.88 (d, 1H), 4.73 (s, 1H), 4.58 (s, 1H), 4.51-4.42 (m, 1H), 4.17-4.06 (m, 1H), 3.80-3.41 (m, 7H), 3.17-3.08 (m, 1H), 2.93-2.84 (m, 1H), 2.50-2.29 (m, 2H), 2.05 (s, 3H), 1.99-1.86 (m, 3H), 1.80-1.02 (m, 22H), 0.95, 0.92 (s, 9H), 0.83 (s, 15H); Mass: [M+Na]+ 693 (100%); M.R: 144.8° C.-156.2° C.

Provenance & Evidence