Hydrochloric Acid → HCID 67777289, Verbindung

HRID 2405513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2405513
[C:1]([O:12][CH2:13][CH2:14][N:15]([CH2:17][CH2:18][NH:19][C:20]([C@:22]12[CH2:60][CH2:59][C@@H:58]([C:61]([CH3:63])=[CH2:62])[C@@H:23]1[C@@H:24]1[C@@:37]([CH3:40])([CH2:38][CH2:39]2)[C@@:36]2([CH3:41])[C@@H:27]([C@:28]3([CH3:57])[C@@H:33]([CH2:34][CH2:35]2)[C:32]([CH3:43])([CH3:42])[C:31]([C:44]2[CH:49]=[CH:48][C:47]([C:50]([O:52]C(C)(C)C)=[O:51])=[CH:46][CH:45]=2)=[CH:30][CH2:29]3)[CH2:26][CH2:25]1)=[O:21])[CH3:16])(=[O:11])[CH2:2][CH2:3][C:4]([O:6]C(C)(C)C)=[O:5].Cl>O1CCOCC1>[C:4]([CH2:3][CH2:2][C:1]([O:12][CH2:13][CH2:14][N:15]([CH3:16])[CH2:17][CH2:18][NH:19][C:20]([C@:22]12[CH2:60][CH2:59][C@@H:58]([C:61]([CH3:63])=[CH2:62])[C@@H:23]1[C@@H:24]1[C@@:37]([CH3:40])([CH2:38][CH2:39]2)[C@@:36]2([CH3:41])[C@@H:27]([C@:28]3([CH3:57])[C@@H:33]([CH2:34][CH2:35]2)[C:32]([CH3:43])([CH3:42])[C:31]([C:44]2[CH:45]=[CH:46][C:47]([C:50]([OH:52])=[O:51])=[CH:48][CH:49]=2)=[CH:30][CH2:29]3)[CH2:26][CH2:25]1)=[O:21])=[O:11])([OH:6])=[O:5]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 67774931HCID 67774931, Verbindung

Produkt 1

HCID 67777289HCID 67777289, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 2-((2-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(tert-butoxycarbonyl)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-carboxamido)ethyl)(methyl)amino)ethyl tert-butyl succinate (40 mg, 0.046 mmol) in dioxane (1 mL) was added 4N HCl (0.115 mL, 0.459 mmol). The reaction mixture was stirred at 20° C. for 3 hours. LCMS indicated the formation of desired product. The reaction mixture was neutralized with 1N NaOH and then filtered. The clear solution was purified by prep HPLC to provide the desired product as colourless oil (7.2 mg, 20%). LCMS: m/e 759.34 (M+H)+, 2.37 min (method 1). 1H NMR (400 MHz, Acetic Acid-d4) δ ppm 7.99 (d, J=8.28 Hz, 2H), 7.26 (d, J=8.53 Hz, 2H), 5.33 (d, J=4.77 Hz, 1H), 4.74 (s, 1H), 4.61 (s, 1H), 4.56-4.44 (m, 2H), 3.90-3.65 (m, 2H), 3.62-3.52 (m, 2H), 3.50-3.38 (m, 2H), 3.19-3.05 (m, 1H), 3.01 (s, 3H), 2.72 (s, 4H), 2.58-2.42 (m, 1H), 2.26-2.11 (m, 2H), 1.69 (s, 3H), 1.96-1.07 (m, 19H), 1.04 (s, 3H), 1.02 (s, 3H), 1.02 (s, 3H), 0.97 (s, 3H), 0.95 (s, 3H).

Quellen und Nachweise

ORD-Eintrag
ord-4ab918c5d94249b09f6320572db78d0c
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802661B2

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