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(1S,4aR,6aS,7R,8R,10aR,10bR,12aR,14R,15R)-14-(acetyloxy)-15-[[(2R)-2,3-dimethyl-2-(methylamino)butyl]oxy]-8-[(1R)-1,2-dimethylpropyl]-1,6,6a,7,8,9,10,10a,10b,11,12,12a-dodecahydro-1,6a,8,10a-tetramethyl-6-oxo-4H-1,4a-propano-2H-phenanthro[1,2-c]pyran-7-carboxylic acid → (1S,4aR,6aS,7R,8R,10aR,10bR,12aR,14R,15R)-15-[[(2R)-2,3-dimethyl-2-(methylamino)butyl]oxy]-8-[(1R)-1,2-dimethylpropyl]-14-[5-[[(1-methylethyl)amino]carbonyl]-1H-1,2,4-triazol-1-yl]-1,6,6a,7,8,9,10,10a,10b,11,12,12a-dodecahydro-1,6a,8,10a-tetramethyl-6-oxo-4H-1,4a-propano-2H-phenanthro[1,2-c]pyran-7-carboxylic acid

HRID 1931549
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1931549
[CH3:1][CH:2]([NH:4][C:5]([C:7]1[N:11]=[CH:10][NH:9][N:8]=1)=[O:6])[CH3:3].C(O[C@@H:16]1[CH2:48][C@:20]23[C:24]4[C@H:33]([CH2:34][CH2:35][C@H:19]2[C@@:18]([CH3:49])([CH2:23][O:22][CH2:21]3)[C@H:17]1[O:50][CH2:51][C@:52]([CH3:58])([NH:56][CH3:57])[CH:53]([CH3:55])[CH3:54])[C@:32]1([CH3:36])[C@:27]([CH3:46])([C@H:28]([C:43]([OH:45])=[O:44])[C@:29]([C@H:38]([CH3:42])[CH:39]([CH3:41])[CH3:40])([CH3:37])[CH2:30][CH2:31]1)[C:26](=[O:47])[CH:25]=4)(=O)C>ClCCCl>[CH3:58][C@@:52]([NH:56][CH3:57])([CH:53]([CH3:55])[CH3:54])[CH2:51][O:50][C@@H:17]1[C@@:18]2([CH3:49])[C@@H:19]3[CH2:35][CH2:34][C@H:33]4[C:24]([C@@:20]3([CH2:21][O:22][CH2:23]2)[CH2:48][C@H:16]1[N:8]1[C:7]([C:5]([NH:4][CH:2]([CH3:1])[CH3:3])=[O:6])=[N:11][CH:10]=[N:9]1)=[CH:25][C:26](=[O:47])[C@:27]1([CH3:46])[C@:32]4([CH3:36])[CH2:31][CH2:30][C@@:29]([C@H:38]([CH3:42])[CH:39]([CH3:40])[CH3:41])([CH3:37])[C@H:28]1[C:43]([OH:45])=[O:44]
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Komponenten

4

Edukt 2

HCID 17751055(1S,4aR,6aS,7R,8R,10aR,10bR,12aR,14R,15R)-14-(acetyloxy)-15-[[(2R)-2,3-dimethyl-2-(methylamino)butyl]oxy]-8-[(1R)-1,2-dimethylpropyl]-1,6,6a,7,8,9,10,10a,10b,11,12,12a-dodecahydro-1,6a,8,10a-tetramethyl-6-oxo-4H-1,4a-propano-2H-phenanthro[1,2-c]pyran-7-carboxylic acidHCID 178457753HCID 178457753, Verbindung

Produkt 1

HCID 68658617
(1S,4aR,6aS,7R,8R,10aR,10bR,12aR,14R,15R)-15-[[(2R)-2,3-dimethyl-2-(methylamino)butyl]oxy]-8-[(1R)-1,2-dimethylpropyl]-14-[5-[[(1-methylethyl)amino]carbonyl]-1H-1,2,4-triazol-1-yl]-1,6,6a,7,8,9,10,10a,10b,11,12,12a-dodecahydro-1,6a,8,10a-tetramethyl-6-oxo-4H-1,4a-propano-2H-phenanthro[1,2-c]pyran-7-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

N-(1-methylethyl)-1H-1,2,4-triazole-3-carboxamide (82.3 mg, 0.534 mmol) and BF3OEt2 (200 μl, 1.578 mmol) were added to a stirred solution of (1S,4aR,6aS,7R,8R,10aR,10bR,12aR,14R,15R)-14-(acetyloxy)-15-[[(2R)-2,3-dimethyl-2-(methylamino)butyl]oxy]-8-[(1R)-1,2-dimethylpropyl]-1,6,6a,7,8,9,10,10a,10b,11,12,12a-dodecahydro-1,6a,8,10a-tetramethyl-6-oxo-4H-1,4a-propano-2H-phenanthro[1,2-c]pyran-7-carboxylic acid (free base form of Example 152 in WO2007127012, herein incorporated by reference in its entirety, 70.2 mg, 0.107 mmol) in 1,2-dichloroethane (1.5 ml). The reaction mixture was a light amber solution that was heated to 50° C. After 50 hours, the reaction mixture was cooled to room temperature, the solvent was evaporated under reduced pressure, and the resulting residue was placed under high vacuum. The residue was dissolved in methanol and purified using two HPLC runs (˜35 mg/run) on a 19×150 mm Sunfire Prep C18 OBD 10 μm column by eluting with acetonitrile/water+0.1% TFA. The total flow rate was 15 ml/min and the HPLC method employed a 12 minute 20%-100% acetonitrile/water gradient followed by a 7 minute acetonitrile flush. The product HPLC fractions were combined, the solvent was evaporated under reduced pressure, and the residue was lyophilized from ethanol and benzene to give the title compound (24.2 mg, 0.028 mmol) as a white solid.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in methanol
  4. custompurified
  5. washby eluting with acetonitrile/water+0.1% TFA
  6. waitThe total flow rate was 15 ml/min and the HPLC method employed a 12 minute
  7. wait20%-100% acetonitrile/water gradient followed by a 7 minute
  8. customacetonitrile flush
  9. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-60d1655f88fc4d0dbde5ffa79f6099ad
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08188085B2

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