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Acetone → (2S,3S,4R,5R)-5-(6-[(2,2-Diphenylethyl)amino]-2-{[({[2-(1-piperidinyl)ethyl]amino}carbonyl)amino]methyl}-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide

HRID 897075
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 897075
C(=O)([O-])[O-].[K+].[K+].C([O:15][C@H:16]1[C@@H:20]([O:21]C(=O)C2C=CC=CC=2)[C@H:19]([N:30]2[CH:38]=[N:37][C:36]3[C:31]2=[N:32][C:33]([CH2:54][NH:55][C:56]([NH:58][CH2:59][CH2:60][N:61]2[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]2)=[O:57])=[N:34][C:35]=3[NH:39][CH2:40][CH:41]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:18][C@@H:17]1[C:67]([NH:69][CH2:70][CH3:71])=[O:68])(=O)C1C=CC=CC=1.CC(C)=O>CO>[C:42]1([CH:41]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH2:40][NH:39][C:35]2[N:34]=[C:33]([CH2:54][NH:55][C:56]([NH:58][CH2:59][CH2:60][N:61]3[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]3)=[O:57])[N:32]=[C:31]3[C:36]=2[N:37]=[CH:38][N:30]3[C@@H:19]2[O:18][C@H:17]([C:67]([NH:69][CH2:70][CH3:71])=[O:68])[C@@H:16]([OH:15])[C@H:20]2[OH:21])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1
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Komponenten

5

Edukt 3

HCID 180AcetoneHCID 11430Potassium Carbonate2×HCID 58904390(2S,3S,4R,5R)-4-(Benzoyloxy)-5-(6-[(2,2-diphenylethyl)amino]-2-{[({[2-(1-piperidinyl) ethyl]amino}carbonyl)amino]methyl}-9H-Purin-9-yl)-2-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate

Produkt 1

HCID 10305241(2S,3S,4R,5R)-5-(6-[(2,2-Diphenylethyl)amino]-2-{[({[2-(1-piperidinyl)ethyl]amino}carbonyl)amino]methyl}-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide
Ausbeute 19,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Potassium carbonate (20 mg, 0.14 mmol) was added to a solution of (2S,3S,4R,5R)-4-(benzoyloxy)-5-(6-[(2,2-diphenylethyl)amino]-2-{[({[2-(1-piperidinyl)ethyl]amino}carbonyl)amino]methyl}-9H-purin-9-yl)-2-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate (100 mg, 0.13 mmol) (Preparation 14) in methanol (100 ml). The reaction mixture was stirred at room temperature for 2 hours. More potassium carbonate (20 mg, 0.14 mmol) was then added and the reaction mixture was heated to 60° C. for 2 hours. The solvent was removed under reduced pressure to give a residue that was slurried with acetone and filtered. The filtrate was evaporated under reduced pressure and the residue was partially purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (90:10:1 by volume). The residue after solvent evaporation under reduced pressure was repurified by more column chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (90:10:1 by volume). The solvent was removed by evaporation under reduced pressure to give the title compound as a foam (17 mg).

Aufarbeitung

  1. temperaturethe reaction mixture was heated to 60° C. for 2 hours
  2. customThe solvent was removed under reduced pressure
  3. customto give a residue that
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. customthe residue was partially purified by column chromatography on silica gel eluting with dichloromethane
  7. customThe residue after solvent evaporation under reduced pressure
  8. customwas repurified by more column chromatography on silica gel eluting with dichloromethane
  9. customThe solvent was removed by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9f74dbb77ee84360b5cce84545194b90
Quelldatensatz
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06921753B2

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