Boronic Acid → (1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-[4-(1-carboxycyclopropyl)phenyl]-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylic acid

HRID 406867Notes

Reaction equation

C(CC[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13]([CH3:43])([CH3:42])[C@H:14]3[C@:27]([CH3:30])([CH2:28][CH:29]=2)[C@@H:26]2[C@:17]([CH3:41])([C@@:18]4([CH3:40])[C@H:23]([CH2:24][CH2:25]2)[C@H:22]2[C@H:31]([C:34]([CH3:36])=[CH2:35])[CH2:32][CH2:33][C@:21]2([C:37]([OH:39])=[O:38])[CH2:20][CH2:19]4)[CH2:16][CH2:15]3)=[CH:8][CH:7]=1)(O)=O.B(C1C=CC([C:53]2([C:56]([OH:58])=[O:57])[CH2:55][CH2:54]2)=CC=1)(O)O.B(O)O>>[C:56]([C:53]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[C:13]([CH3:43])([CH3:42])[C@H:14]4[C@:27]([CH3:30])([CH2:28][CH:29]=3)[C@@H:26]3[C@:17]([CH3:41])([C@@:18]5([CH3:40])[C@H:23]([CH2:24][CH2:25]3)[C@H:22]3[C@H:31]([C:34]([CH3:36])=[CH2:35])[CH2:32][CH2:33][C@:21]3([C:37]([OH:39])=[O:38])[CH2:20][CH2:19]5)[CH2:16][CH2:15]4)=[CH:10][CH:11]=2)[CH2:55][CH2:54]1)([OH:58])=[O:57]

Participants

Reactant 3

HCID 61668Boronic Acid

HCID 467396661-(4-Boronophenyl)cyclopropane-1-carboxylic acid

HCID 54761941(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-[4-(2-carboxyethyl)phenyl]-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylic acid

Product 1

HCID 54762135(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-[4-(1-carboxycyclopropyl)phenyl]-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylic acid

Procedure

The title compound was prepared following the methods 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 1-(4-boronophenyl)cyclopropanecarboxylic acid as the reactant boronic acid. The product was isolated as a white solid (1.76 mg, 5%). LCMS: m/e 597.64 (M−H)−, 4.43 min (method 2). 1H NMR (599 MHz, DMSO-D6_CDCl3) δ ppm 0.92 (s, 3H), 0.94 (s, 3H), 0.99 (d, J=3.52 Hz, 6H), 1.02 (s, 3H), 1.03-1.71 (m, 21H), 1.71 (s, 3H), 1.82-1.95 (m, 2H), 2.10 (dd, J=17.28, 6.15 Hz, 1H), 2.20 (d, J=12.30 Hz, 1H), 2.30-2.39 (m, 1H), 2.97-3.09 (m, 1H), 4.61 (br. s, 1H), 4.74 (s, 1H), 5.25 (d, J=4.69 Hz, 1H), 7.04 (d, J=7.62 Hz, 2H), 7.25 (d, J=7.62 Hz, 2H).

Sources & evidence

ORD record: ord-23e1eee699b3448683cc992797d3b609
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754068B2

Reaction notes

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