Boronic Acid → (1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-[4-[(E)-3-hydroxy-3-oxo-prop-1-enyl]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 406872Notes

Reaction equation

[C:1]([CH2:4][CH2:5][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)([OH:3])=[O:2].B(C1C=CC(/C=C/C(O)=O)=CC=1)(O)O.B(O)O>>[C:1](/[CH:4]=[CH:5]/[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)([OH:3])=[O:2]

Participants

Reactant 3

HCID 61668Boronic Acid

HCID 52880014-(Carboxyvin-2-Yl)Phenylboronic 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 54759389(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-[4-[(E)-3-hydroxy-3-oxo-prop-1-enyl]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 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 (E)-3-(4-boronophenyl)acrylic acid as the reactant boronic acid. The product was isolated as a white solid (3.65 mg, 11%). LCMS: m/e 583.60 (M−H)−, 5.03 min (method 2). 1H NMR (599 MHz, DMSO-D6_CDCl3) δ ppm 0.94 (d, J=3.52 Hz, 6H), 1.00 (s, 6H), 1.02 (s, 3H), 1.03-1.76 (m, 17H), 1.71 (s, 3H), 1.88 (d, J=7.03 Hz, 2H), 2.08-2.16 (m, 1H), 2.20 (d, J=12.30 Hz, 1H), 2.30-2.40 (m, 1H), 3.02 (d, J=5.27 Hz, 1H), 4.61 (s., 1H), 4.74 (s, 1H), 5.28 (d, J=4.69 Hz, 1H), 6.49 (d, J=15.82 Hz, 1H), 7.17 (d, J=8.20 Hz, 2H), 7.54-7.71 (m, 3H).

Sources & evidence

ORD record: ord-b9f41fb17dfa40068535842da4ad99eb
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754068B2

Reaction notes

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