Ethanol → HCID 77461006, compound

HRID 1773043Notes

Reaction equation

[CH3:1][C@:2]12[C@@:19]3([CH3:20])[C@@H:10]([C@:11]4([CH3:30])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:22])([CH3:21])[C:14]([CH:23]=[C:24]3[CH2:27]C(C#N)[CH2:25]3)=[CH:13][CH2:12]4)[CH2:9][CH2:8][C@@H:7]1[C@H:6]1[C@H:31]([C:34]([CH3:36])=[CH2:35])[CH2:32][CH2:33][C@:5]1([NH:37][CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][CH:43]([S:46]([CH3:49])(=[O:48])=[O:47])[CH2:42][CH2:41]1)[CH2:4][CH2:3]2.[OH-:50].[K+].[CH2:52]([OH:54])[CH3:53]>>[CH3:1][C@:2]12[C@@:19]3([CH3:20])[C@@H:10]([C@:11]4([CH3:30])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:22])([CH3:21])[C:14]([CH:23]=[C:24]3[CH2:27][CH:53]([C:52]([OH:50])=[O:54])[CH2:25]3)=[CH:13][CH2:12]4)[CH2:9][CH2:8][C@@H:7]1[C@H:6]1[C@H:31]([C:34]([CH3:36])=[CH2:35])[CH2:32][CH2:33][C@:5]1([NH:37][CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][CH:43]([S:46]([CH3:49])(=[O:48])=[O:47])[CH2:42][CH2:41]1)[CH2:4][CH2:3]2

Participants

Reactant 3

HCID 702Ethanol

HCID 14797Potassium Hydroxide

HCID 86731501HCID 86731501, compound

Product 1

HCID 77461006HCID 77461006, compoundYield 29.2%

Conditions

Temperature: 76 °C

Procedure

To a solution of 3-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)-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]chrysen-9-yl)methylene)cyclobutanecarbonitrile (30 mg, 0.043 mmol) in ethanol (2 mL) was added potassium hydroxide (1 mL, 0.043 mmol). A white precipitate was formed. The mixture became clear after warming up to 76° C. The reaction solution was stirred at 76° C. for 7 h. The crude product was purified without further work up by prep HPLC (method 4) to give 3-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)-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]chrysen-9-yl)methylene)cyclobutanecarboxylic acid as a white solid (9 mg, 29.2%). MS: m/e 709.55 (M+H)+, 2.54 min (method 4). 1H NMR (400 MHz, METHANOL-d4) δ 5.72 (br. s., 1H), 5.38 (d, J=5.5 Hz, 1H), 4.78 (s, 1H), 4.68 (s, 1H), 3.28-2.75 (m, 14H), 2.96 (s, 3H), 2.65-2.52 (m, 1H), 2.42-2.27 (m, 1H), 2.23-1.80 (m, 11H), 1.75 (s, 3H), 1.69-1.27 (m, 14H), 1.22 (s, 3H), 1.10 (br. s., 3H), 1.01 (br. s., 3H), 0.96-0.93 (m, 3H), 0.90-0.87 (m, 3H).

Workup

customA white precipitate was formed
customThe crude product was purified

Sources & evidence

ORD record: ord-135b7177ee474aa3960ea2cad0c3d9c2
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249180B2

Reaction notes

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