Boronic Acid → HCID 54759763, 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.B([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1/[CH:53]=[CH:54]/[C:55]([OH:57])=[O:56])(O)O.B(O)O>>[C:55]([CH2:54][CH2:53][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=1[C:12]1[C:13]([CH3:43])([CH3:42])[C@H:14]2[C@:27]([CH3:30])([CH2:28][CH:29]=1)[C@@H:26]1[C@:17]([CH3:41])([C@@:18]3([CH3:40])[C@H:23]([CH2:24][CH2:25]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]3)[CH2:16][CH2:15]2)([OH:57])=[O:56]Participants
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 (E)-3-(2-boronophenyl)acrylic acid as the reactant boronic acid. The product was isolated as a white solid (37.4 mg, 86%). LCMS: m/e 585.58 (M−H)−, 6.84 min (method 3). 1H NMR (400 MHz, <DMSOmix>) δ ppm 0.80 (d, 3H), 0.98 (s, 6H), 1.00 (s, 6H), 1.04-1.73 (m, 17H), 1.68 (s, 3H), 1.79-1.96 (m, 2H), 2.00-2.23 (m, 2H), 2.27-2.37 (m, 1H), 2.71-2.83 (m, 2H), 2.84-2.95 (m, 2H), 2.96-3.05 (m, 1H), 4.59 (s, 1H), 4.72 (s, 1H), 5.24 (d, J=4.98 Hz, 1H), 6.97-7.06 (m, 1H), 7.06-7.14 (m, 1H), 7.14-7.30 (m, 2H).
Sources & evidence
- ORD record
- ord-35f85fa5c2a045258bc10e171591cc66
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754068B2
Reaction notes
Loading…