Boronic Acid → HCID 54759585, compound
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.[CH3:44][S:45]([C:48]1[CH:53]=[CH:52][C:51](B(O)O)=[CH:50][CH:49]=1)(=[O:47])=[O:46].B(O)O>>[CH3:40][C@:18]12[C@@:17]3([CH3:41])[C@@H:26]([C@:27]4([CH3:30])[C@@H:14]([CH2:15][CH2:16]3)[C:13]([CH3:42])([CH3:43])[C:12]([C:51]3[CH:52]=[CH:53][C:48]([S:45]([CH3:44])(=[O:47])=[O:46])=[CH:49][CH:50]=3)=[CH:29][CH2:28]4)[CH2:25][CH2:24][C@@H:23]1[C@H:22]1[C@H:31]([C:34]([CH3:36])=[CH2:35])[CH2:32][CH2:33][C@:21]1([C:37]([OH:39])=[O:38])[CH2:20][CH2:19]2Participants
Reactant 3
Product 1
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 4-(methylsulfonyl)phenylboronic acid as the reactant boronic acid. The product was isolated as a white solid (3.5 mg, 20%). LCMS: m/e 591.61 (M−H)−, 6.74 min (method 3). 1H NMR (400 MHz, <DMSOmix>) δ ppm 0.92 (s, 6H), 0.98 (s, 6H), 1.00 (s, 3H), 1.02-1.77 (m, 17H), 1.68 (s, 3H), 1.79-1.97 (m, 2H), 2.05-2.23 (m, 2H), 2.32 (t, J=13.47 Hz, 1H), 2.90-3.06 (m, 1H), 3.19 (s, 3H), 4.58 (s, 1H), 4.71 (s, 1H), 5.29 (d, J=5.57 Hz, 1H), 7.36 (d, J=6.44 Hz, 2H), 7.85 (d, J=8.20 Hz, 2H).
Sources & evidence
- ORD record
- ord-f9ac32370b3f4e91985b437ba451199f
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754068B2
Reaction notes
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