Ammonia → (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(9H-fluoren-9-ylmethyl)amino]-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydro-3,4-furandiol

HRID 1293028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1293028
N.C([O:5][C@H:6]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][C:18]([C:39]#[N:40])=[N:19][C:20]=3[NH:24][CH2:25][CH:26]2[C:38]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:32]3[C:27]2=[CH:28][CH:29]=[CH:30][CH:31]=3)[O:8][C@@H:7]1[CH2:41][O:42]C(=O)C)(=O)C>C(O)C.[Pd]>[NH2:40][CH2:39][C:18]1[N:17]=[C:16]2[C:21]([N:22]=[CH:23][N:15]2[C@H:9]2[C@H:10]([OH:11])[C@H:6]([OH:5])[C@@H:7]([CH2:41][OH:42])[O:8]2)=[C:20]([NH:24][CH2:25][CH:26]2[C:38]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:32]3[C:27]2=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:19]=1

Komponenten

5

Edukt 2

HCID 222AmmoniaHCID 60018587(2R,3R,4R,5R)-4-(Acetyloxy)-2-[(acetyloxy)methyl]-5-{2-cyano-6-[(9H-fluoren-9-ylmethyl) amino]-9H-purin-9-yl}tetrahydro-3-furanyl acetate

Produkt 1

HCID 60018582(2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(9H-fluoren-9-ylmethyl)amino]-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydro-3,4-furandiolAusbeute 37,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Ammonia gas was passed through an ice cold solution of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-{2-cyano-6-[(9H-fluoren-9-ylmethyl)amino]-9H-purin-9-yl}tetrahydro-3-furanyl acetate (1.2 g, 2 mmol) (Preparation 71) in ethanol (40 ml) until the solution was saturated. 10% Palladium on carbon (120 mg) was added and the reaction mixture was stirred under an atmosphere of hydrogen gas (413.7 kPa, 60 psi) at room temperature for 40 hours. The suspension was filtered through Arbocel (Trade Mark) and the solvent was removed from the filtrate under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (96:4:0.4 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (94:6:0.5 by volume). The solvent was removed under reduced pressure to give the title compound (358 mg) as a foam.

Aufarbeitung

  1. filtrationThe suspension was filtered through Arbocel (Trade Mark)
  2. customthe solvent was removed from the filtrate under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane
  4. temperaturemethanol:0.88 concentrated aqueous ammonia (96:4:0.4 by volume) increasing in polarity to dichloromethane
  5. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f292a6f2b0444927896c5e3d86817f07
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238676B2

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