Sodium Hydroxide → HCID 86676645, Verbindung

HRID 85744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 85744
[CH3:1][N:2]([CH3:55])[C:3](=[O:54])[C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][NH:14][C@:15]23[CH2:50][CH2:49][C@@H:48]([C:51]([CH3:53])=[CH2:52])[C@@H:16]2[C@@H:17]2[C@@:30]([CH3:33])([CH2:31][CH2:32]3)[C@@:29]3([CH3:34])[C@@H:20]([C@:21]4([CH3:47])[C@@H:26]([CH2:27][CH2:28]3)[C:25]([CH3:36])([CH3:35])[C:24]([C:37]3[CH:46]=[CH:45][C:40]([C:41]([O:43]C)=[O:42])=[CH:39][CH:38]=3)=[CH:23][CH2:22]4)[CH2:19][CH2:18]2)[CH2:8][CH2:7]1)=[O:5].[OH-].[Na+]>O1CCOCC1>[CH3:55][N:2]([CH3:1])[C:3](=[O:54])[C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][NH:14][C@:15]23[CH2:50][CH2:49][C@@H:48]([C:51]([CH3:53])=[CH2:52])[C@@H:16]2[C@@H:17]2[C@@:30]([CH3:33])([CH2:31][CH2:32]3)[C@@:29]3([CH3:34])[C@@H:20]([C@:21]4([CH3:47])[C@@H:26]([CH2:27][CH2:28]3)[C:25]([CH3:36])([CH3:35])[C:24]([C:37]3[CH:38]=[CH:39][C:40]([C:41]([OH:43])=[O:42])=[CH:45][CH:46]=3)=[CH:23][CH2:22]4)[CH2:19][CH2:18]2)[CH2:8][CH2:7]1)=[O:5]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 86676646methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(4-(2-(dimethylamino)-2-oxoacetyl)piperazin-1-yl)ethyl)amino)-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]chrysen-9-yl)benzoate

Produkt 1

HCID 86676645HCID 86676645, VerbindungAusbeute 43,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
82 °C

Versuchsvorschrift

A mixture of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(4-(2-(dimethylamino)-2-oxoacetyl)piperazin-1-yl)ethyl)amino)-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]chrysen-9-yl)benzoate (40 mg, 0.053 mmol) and sodium hydroxide (0.530 mL, 0.530 mmol) in dioxane (1 mL) was heated up at 82° C. for 3 hours. The reaction mixture was cooled to room temperature, filtered and the clear solution was purified by HPLC to provide the title compound as a white solid (17 mg, 41%). LCMS: m/e 741.65 (M+H)+, 2.29 min (method 11). 1H NMR (400 MHz, Acetic) δ 7.99 (d, J=8.3 Hz, 2H), 7.26 (d, J=8.3 Hz, 2H), 5.33 (d, J=4.5 Hz, 1H), 4.82 (s, 1H), 4.71 (s, 1H), 4.14-3.78 (m, 2H), 3.75-3.36 (m, 6H), 3.22 (br. s., 4H), 3.03 (s, 3H), 3.00 (s, 3H), 2.92-2.75 (m, 1H), 2.29-1.05 (m, 22H), 1.73 (s, 3H), 1.20 (s, 3H), 1.10 (s, 3H), 1.05 (s, 3H), 0.98 (s, 3H), 0.96 (s, 3H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customthe clear solution was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9d55fe20b8ce431f975ef88c8a6a6b44
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846647B2

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