Boronic Acid → (1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-[4-[(4-hydroxy-4-oxo-butanoyl)amino]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 406866Notes

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([NH:53][C:54](=[O:60])[CH2:55][CH2:56][C:57]([OH:59])=[O:58])=CC=1)(O)O.B(O)O>>[C:57]([CH2:56][CH2:55][C:54]([NH:53][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13]([CH3:42])([CH3:43])[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:60])([OH:59])=[O:58]

Participants

Reactant 3

HCID 61668Boronic Acid

HCID 27693934-((4-Boronophenyl)amino)-4-oxobutanoic 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 54762134(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-[4-[(4-hydroxy-4-oxo-butanoyl)amino]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 (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-(4-boronophenylamino)-4-oxobutanoic acid as the reactant boronic acid. The product was isolated as a white solid (2.98 mg, 9%). LCMS: m/e 628.63 (M−H)−, 3.71 min (method 2). 1H NMR (599 MHz, DMSO-D6_CDCl3) δ ppm 0.91 (s, 3H), 0.93 (s, 3H), 0.98 (s, 3H), 0.99 (s, 3H), 1.02 (s, 3H), 1.03-1.71 (m, 17H), 1.71 (s, 3H), 1.84-1.93 (m, 2H), 2.09 (dd, J=17.87, 5.57 Hz, 1H), 2.20 (d, J=12.30 Hz, 1H), 2.29-2.39 (m, 1H), 2.59-2.62 (m, 2H), 2.97-3.10 (m, 1H), 3.30-3.33 (m, 2H), 4.61 (br. s, 1H), 4.74 (s, 1H), 5.24 (d, J=5.27 Hz, 1H), 7.03 (d, J=8.79 Hz, 2H), 7.51 (d, J=8.20 Hz, 2H).

Sources & evidence

ORD record: ord-6ec186093cea44d7a60acd3fe2ec8c9f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754068B2

Reaction notes

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