(Cyclohexylamino)(oxo)acetic acid → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(cyclohexylamino)-2-oxoacetamido)-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]chrysen-9-yl)benzoic acid

Beteiligte Stoffe

Reaktionsschritte

The title compound was prepared in 40% yield from methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-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]chrysen-9-yl)benzoate following the same procedure as described for the preparation of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(3-(dimethylamino)propanamido)-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]chrysen-9-yl)benzoic acid, except 2-(cyclohexylamino)-2-oxoacetic acid was used instead of 3-(dimethylamino)propionic acid hydrochloride in Step 1. LCMS: m/e 681.7 (M−H)−, 2.42 min (method 9). 1H NMR (500 MHz, CHLOROFORM-d) δ=8.03 (d, J=8.5 Hz, 2H), 7.61 (s, 1H), 7.52 (d, J=8.5 Hz, 1H), 7.25 (d, J=8.2 Hz, 2H), 6.51 (br. s., 1H), 5.33 (d, J=4.6 Hz, 1H), 4.79 (d, J=1.2 Hz, 1H), 4.67 (s, 1H), 3.83-3.72 (m, 1H), 2.62-2.54 (m, 2H), 2.50 (dd, J=8.5, 11.6 Hz, 1H), 2.14 (dd, J=6.3, 17.2 Hz, 1H), 2.00-1.89 (m, 3H), 1.86-1.75 (m, 4H), 1.71-1.62 (m, 2H), 1.61-1.36 (m, 13H), 1.35-1.20 (m, 5H), 1.18-1.11 (m, 2H), 1.08 (s, 3H), 1.05-1.02 (m, 3H), 1.00 (s, 3H), 0.96 (s, 6H).

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