Boronic Acid → HCID 54759584, compound

HRID 406873

Reaction equation

HRID 406873 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.[N:44]1[NH:45][N:46]=[N:47][C:48]=1[C:49]1[CH:50]=[C:51](B(O)O)[CH:52]=[CH:53][CH:54]=1.B(O)O>>[N:44]1[NH:45][N:46]=[N:47][C:48]=1[C:49]1[CH:50]=[C:51]([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:53][CH:54]=1

Participants

4

Reactant 3

HCID 61668Boronic AcidHCID 467379963-(Tetrazol-5-yl)phenylboronic acidHCID 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 54759584HCID 54759584, 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 3-(2H-tetrazol-5-yl)phenylboronic acid as the reactant boronic acid. The product was isolated as a white solid (4.56 mg, 26%). LCMS: m/e 581.53 (M−H)−, 4.12 min (method 3). 1H NMR (400 MHz, <DMSOmix>) δ ppm 0.95 (d, J=4.10 Hz, 6H), 0.99 (s, 3H), 1.01 (s, 6H), 1.03-1.76 (m, 17H), 1.69 (s, 3H), 1.81-1.93 (m, 2H), 2.07-2.23 (m, 2H), 2.34 (dd, J=13.47, 2.34 Hz, 1H), 2.95-3.06 (m, 1H), 4.58 (s, 1H), 4.72 (s, 1H), 5.32 (d, J=4.39 Hz, 1H), 7.22 (d, J=6.44 Hz, 1H), 7.38-7.51 (m, 1H), 7.81 (s, 1H), 7.92 (d, J=7.32 Hz, 1H).

Sources & evidence

ORD record
ord-3a6a6a3a14db43b28fe62b7c28861087
Source dataset
uspto-grants-2014_06
Patent number
US08754068B2

Linked notes

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