Boronic Acid → HCID 54759764, compound

HRID 406877Notes

Reaction equation

HRID 406877 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([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:8][CH:7]=1)([OH:3])=[O:2].B(C1C=CC([C:53]2C=C(C(O)=O)[C:60]3[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=3)[N:54]=2)=CC=1)(O)O.B(O)O>>[C:37]([C@:21]12[CH2:33][CH2:32][C@@H:31]([C:34]([CH3:36])=[CH2:35])[C@@H:22]1[C@@H:23]1[C@@:18]([CH3:40])([CH2:19][CH2:20]2)[C@@:17]2([CH3:41])[C@@H:26]([C@:27]3([CH3:30])[C@@H:14]([CH2:15][CH2:16]2)[C:13]([CH3:43])([CH3:42])[C:12]([C:9]2[CH:10]=[CH:11][C:6]([C:5]4[CH:53]=[N:54][C:55]5[C:60]([C:4]=4[C:1]([OH:3])=[O:2])=[CH:59][CH:58]=[CH:57][CH:56]=5)=[CH:7][CH:8]=2)=[CH:29][CH2:28]3)[CH2:25][CH2:24]1)([OH:39])=[O:38]

Participants

4

Reactant 3

HCID 61668Boronic AcidHCID 27343402-(4-boronophenyl)quinoline-4-carboxylic 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 54759764HCID 54759764, 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 2-(4-boronophenyl)quinoline-4-carboxylic acid as the reactant boronic acid. The product was isolated as a white solid (4.7 mg, 27%). LCMS: m/e 684.65 (M−H)−, 5.11 min (method 3). 1H NMR (400 MHz, <DMSOmix>) δ ppm 0.95-1.00 (m, 9H), 1.01 (s, 6H), 1.05-1.77 (m, 17H), 1.69 (s, 3H), 1.80-1.94 (m, 2H), 2.07-2.23 (m, 2H), 2.31-2.38 (m, 1H), 2.94-3.06 (m, 1H), 4.59 (s, 1H), 4.72 (s, 1H), 5.33 (d, J=6.15 Hz, 1H), 7.30 (d, J=7.32 Hz, 2H), 7.59-7.67 (m, 1H), 7.74-7.84 (m, 1H), 8.08-8.14 (m, 1H), 8.18 (d, J=8.79 Hz, 2H), 8.32-8.42 (m, 1H), 8.72 (d, J=6.15 Hz, 1H).

Sources & evidence

ORD record
ord-cfd687885caa46618d2e6fc687886785
Source dataset
uspto-grants-2014_06
Patent number
US08754068B2

Reaction notes

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