Boronic Acid → HCID 54759762, compound

HRID 406875Notes

Reaction equation

C(CCC1C=CC([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)=CC=1)(O)=O.B([C:47]1[CH:48]=[C:49](/[CH:53]=[CH:54]/[C:55]([OH:57])=[O:56])[CH:50]=[CH:51][CH:52]=1)(O)O.B(O)O>>[C:55]([CH2:54][CH2:53][C:49]1[CH:48]=[C:47]([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:52]=[CH:51][CH:50]=1)([OH:57])=[O:56]

Participants

Reactant 3

HCID 61668Boronic Acid

HCID 58448763-(2-Carboxyvinyl)benzeneboronic 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 54759762HCID 54759762, compound

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-(3-boronophenyl)acrylic acid as the reactant boronic acid. The product was isolated as a white solid (34.4 mg, 80%). LCMS: m/e 585.63 (M−H)−, 6.47 min (method 3). 1H NMR (400 MHz, <DMSOmix>) δ ppm 0.89 (d, 6H), 0.97 (s, 6H), 1.00 (s, 3H), 1.01-1.66 (m, 17H), 1.68 (s, 3H), 1.80-1.94 (m, 2H), 2.02-2.12 (m, 1H), 2.13-2.22 (m, 1H), 2.26-2.39 (m, 1H), 2.55-2.60 (m, 2H), 2.83 (t, J=7.62 Hz, 2H), 2.94-3.07 (m, 1H), 4.58 (br. s., 1H), 4.71 (s, 1H), 5.20 (d, J=4.10 Hz, 1H), 6.88-6.98 (m, 2H), 7.08 (d, J=6.44 Hz, 1H), 7.13-7.22 (m, 1H).

Sources & evidence

ORD record: ord-fb5754ab488e48e8ac699ed5b5b8c051
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754068B2

Reaction notes

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