Sodium Carbonate → N-{2-[Cyclopentyl(isopropyl)amino]ethyl}-N'-({6-[(2,2-diphenylethyl)amino]-9-[(2R,3R,4S,5R)-5-(2-ethyl-2H-tetrazol-5-yl)-3,4-dihydroxytetrahydro-2-furanyl]-9H-purin-2-yl}methyl)urea

HRID 1168277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1168277
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([CH2:45][NH:46][C:47]([NH:49][CH2:50][CH2:51][N:52]([CH:56]1[CH2:60][CH2:59][CH2:58][CH2:57]1)[CH:53]([CH3:55])[CH3:54])=[O:48])=[N:25][C:26]=2[NH:30][CH2:31][CH:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH:56]1([N:52]([CH:53]([CH3:54])[CH3:55])[CH2:51][CH2:50][NH:49][C:47]([NH:46][CH2:45][C:24]2[N:23]=[C:22]3[C:27]([N:28]=[CH:29][N:21]3[C@H:6]3[C@H:5]([OH:4])[C@H:9]([OH:10])[C@@H:8]([C:14]4[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=4)[O:7]3)=[C:26]([NH:30][CH2:31][CH:32]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:25]=2)=[O:48])[CH2:57][CH2:58][CH2:59][CH2:60]1

Komponenten

4

Edukt 2

HCID 10340Sodium CarbonateHCID 69978470(2R,3R,4R,5R)-4-(Acetoxy)-2-{2-({[({2-[cyclopentyl(isopropyl)-amino]ethyl}amino)carbonyl]amino}methyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl Acetate

Produkt 1

HCID 10305826N-{2-[Cyclopentyl(isopropyl)amino]ethyl}-N'-({6-[(2,2-diphenylethyl)amino]-9-[(2R,3R,4S,5R)-5-(2-ethyl-2H-tetrazol-5-yl)-3,4-dihydroxytetrahydro-2-furanyl]-9H-purin-2-yl}methyl)ureaAusbeute 29,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (2R,3R,4R,5R)-4-(acetoxy)-2-{2-({[({2-[cyclopentyl(isopropyl)amino]ethyl}amino)carbonyl]amino}methyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl acetate (Preparation 45) (135 mg, 0.16 mmol) and sodium carbonate (5 mg, 0.05 mmol) in methanol (5 ml) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:conc. aqueous ammonia (95:5:0.5 by volume) gradually changing to dichloromethane:methanol:conc. aqueous ammonia (90:10:1 by volume). Product containing fractions were evaporated and the resulting solid was dried under vacuum to afford the title compound as a white powder (35 mg).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane
  3. additionProduct containing fractions
  4. customwere evaporated
  5. customthe resulting solid was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ca367d2964cf4325b7d696f35d7fe974
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06624158B2

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