Boronic Acid → (1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-hydroxyphenyl)-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 406870Notes

Reaction equation

HRID 406870 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.[OH:44][C:45]1[CH:50]=[CH:49][C:48](B(O)O)=[CH:47][CH:46]=1.B(O)O>>[OH:44][C:45]1[CH:50]=[CH:49][C:48]([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:47][CH:46]=1

Participants

4

Reactant 3

HCID 61668Boronic AcidHCID 27343604-Hydroxyphenylboronic 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 54759387(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-hydroxyphenyl)-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 4-hydroxyphenylboronic acid as the reactant boronic acid. The product was isolated as a white solid (1.25 mg, 4%). LCMS: m/e 529.55 (M−H)−, 4.34 min (method 2).

Sources & evidence

ORD record
ord-f59e0ea79f3e4503a90e0be43296bb70
Source dataset
uspto-grants-2014_06
Patent number
US08754068B2

Reaction notes

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