(1H-1,2,3-Triazol-1-yl)acetic acid--hydrogen chloride (1/1) → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(1H-1,2,3-triazol-1-yl)acetamido)-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

Participants

Reaction Steps

The title compound was prepared in 36% 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 1H-1,2,3-triazole-1-acetic acid hydrochloride was used instead of 3-(dimethylamino)propionic acid hydrochloride in Step 1. LCMS: m/e 639.5 (M+H)+, 2.04 min (method 6). 1H NMR (500 MHz, 1:1 CDCl3:MeOD) δ=7.94 (d, J=0.9 Hz, 1H), 7.92 (d, J=8.5 Hz, 2H), 7.77 (d, J=0.9 Hz, 1H), 7.20 (d, J=8.5 Hz, 2H), 6.93 (s, 1H), 5.29 (dd, J=1.7, 6.3 Hz, 1H), 5.15 (s, 2H), 4.75 (d, J=1.5 Hz, 1H), 4.64 (br. s., 1H), 2.63-2.57 (m, 1H), 2.57-2.50 (m, 1H), 2.37 (dd, J=8.1, 12.7 Hz, 1H), 2.12 (dd, J=6.4, 17.1 Hz, 1H), 1.94-1.83 (m, 1H), 1.78-1.72 (m, 3H), 1.70 (s, 3H), 1.69-1.64 (m, 1H), 1.58-1.39 (m, 8H), 1.38-1.29 (m, 3H), 1.24 (dd, J=3.7, 10.4 Hz, 1H), 1.15-1.06 (m, 2H), 1.02 (s, 3H), 1.01 (s, 3H), 1.00 (s, 3H), 0.94 (s, 3H), 0.93 (s, 3H).

Provenance & Evidence