Trifluoroacetic acid → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(piperidin-3-ylmethylamino)-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)benzoic acid

HRID 85642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 85642
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C@:16]23[CH2:50][CH2:49][C@@H:48]([C:51]([CH3:53])=[CH2:52])[C@@H:17]2[C@@H:18]2[C@@:31]([CH3:34])([CH2:32][CH2:33]3)[C@@:30]3([CH3:35])[C@@H:21]([C@:22]4([CH3:47])[C@@H:27]([CH2:28][CH2:29]3)[C:26]([CH3:37])([CH3:36])[C:25]([C:38]3[CH:46]=[CH:45][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=3)=[CH:24][CH2:23]4)[CH2:20][CH2:19]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:34][C@:31]12[C@@:30]3([CH3:35])[C@@H:21]([C@:22]4([CH3:47])[C@@H:27]([CH2:28][CH2:29]3)[C:26]([CH3:36])([CH3:37])[C:25]([C:38]3[CH:46]=[CH:45][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=3)=[CH:24][CH2:23]4)[CH2:20][CH2:19][C@@H:18]1[C@H:17]1[C@H:48]([C:51]([CH3:53])=[CH2:52])[CH2:49][CH2:50][C@:16]1([NH:15][CH2:14][CH:10]1[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]1)[CH2:33][CH2:32]2

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 683581024-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((1-(tert-butoxycarbonyl)piperidin-3-yl)methylamino)-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)benzoic acid

Produkt 1

HCID 683580824-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(piperidin-3-ylmethylamino)-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)benzoic acidAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((1-(tert-butoxycarbonyl)piperidin-3-yl)methylamino)-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)benzoic acid (0.019 g, 0.026 mmol) in DCM (1 mL) was added TFA (0.25 mL, 3.24 mmol). The mixture was stirred at rt for 1.75 h. Then, the mixture was concentrated under reduced pressure and purified by prep HPLC to give the title compound (14.2 mg, 0.021 mmol, 81% yield) as a white solid. LCMS: m/e 627.6 (M+H)+, 1.50 min (method 2). 1H NMR (500 MHz, Acetic acid d4) δ ppm 8.04 (2H, d, J=8.2 Hz), 7.30 (2H, d, J=7.9 Hz), 5.37 (1H, s), 4.85 (1H, d, J=5.5 Hz), 4.75 (1H, s), 2.98-3.83 (6H, m), 2.82-2.91 (1H, m), 2.57-2.72 (1H, m), 0.85-2.33 (44H, m).

Aufarbeitung

  1. concentrationThen, the mixture was concentrated under reduced pressure
  2. custompurified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9854c6d785904b629e8bd8ee7d188d8a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846647B2

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