Réaction #494050

Équation de réaction

boronic acid

(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(2-carboxyethyl)phenyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid

4-borono-2-fluorobenzoic acid

→

title compound

(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-carboxy-3-fluorophenyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid

Conditions de réaction

Mode opératoire

The title compound was prepared following the method described above for compound (1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(2-carboxyethyl)phenyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid (example 4a) using 4-borono-2-fluorobenzoic acid as the reactant boronic acid. The product was isolated as a white solid (6.46 mg, 19%). LCMS: m/e 575.54 (M−H)−, 3.88 min (method 2). 1H NMR (599 MHz, DMSO-D6_CDCl3) δ ppm 0.95 (s, 6H), 0.98 (s, 3H), 1.00 (s, 3H), 1.02 (s, 3H), 1.04-1.76 (m, 17H), 1.71 (s, 3H), 1.88 (d, J=7.03 Hz, 2H), 2.13 (dd, J=17.58, 6.44 Hz, 1H), 2.20 (d, J=12.30 Hz, 1H), 2.29-2.39 (m, 1H), 2.98-3.07 (m, 1H), 4.61 (s, 1H), 4.74 (s, 1H), 5.33 (d, J=5.27 Hz, 1H), 6.96 (d, J=11.13 Hz, 1H), 7.02 (d, J=8.20 Hz, 1H), 7.79 (t, J=7.62 Hz, 1H).

Source