Hexamethyldisilazane → (2R,3R,4R,5R)-4-(Benzoyloxy)-5-[2-cyano-6-(phenethylamino)-9H-purin-9-yl]-2-(methoxymethyl)tetrahydro-3-furanyl benzoate

HRID 2268431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2268431
[CH2:1]([NH:9][C:10]1[N:18]=[C:17]([C:19]#[N:20])[N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][NH:14]2)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:21]([O:29][C@H:30]1[C@@H:34]([O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:33](OC(=O)C)[O:32][C@@H:31]1[CH2:48][O:49][CH3:50])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[C@H]1[C@@H](OC(=O)C2C=CC=CC=2)[C@@H](OC(=O)C)O[C@@H]1COC)(=O)C1C=CC=CC=1.S([O-])([O-])(=O)=O.[NH4+].[NH4+].C[Si](C)(C)N[Si](C)(C)C.Br[Si](C)(C)C>[Bi](Br)(Br)Br.ClCCl.C(#N)C>[C:21]([O:29][C@H:30]1[C@@H:34]([O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:33]([N:14]2[CH:13]=[N:12][C:11]3[C:15]2=[N:16][C:17]([C:19]#[N:20])=[N:18][C:10]=3[NH:9][CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[O:32][C@@H:31]1[CH2:48][O:49][CH3:50])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

10

Edukt 6

HCID 13838HexamethyldisilazaneHCID 76113BromotrimethylsilaneHCID 6097028Ammonium SulfateHCID 69534087(2R,3R,4R,5R)-5-(acetyloxy)-4-(benzoyloxy)-2-(methoxymethyl)tetrahydro-3-furanyl benzoateHCID 69534095(2R,3R,4R,5S)-5-(acetyloxy)-4-(benzoyloxy)-2-(methoxymethyl)tetrahydro-3-furanyl benzoateHCID 178510600HCID 178510600, Verbindung

Produkt 1

HCID 59975283(2R,3R,4R,5R)-4-(Benzoyloxy)-5-[2-cyano-6-(phenethylamino)-9H-purin-9-yl]-2-(methoxymethyl)tetrahydro-3-furanyl benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 82232bismuth(III) bromideKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The title compound was prepared by a similar method to preparation 11 using 6-(phenethylamino)-9H-purine-2-carbonitrile (3.8 g, 11.2 mmol) (preparation 45), (2R,3R,4R,5S)-5-(acetyloxy)-4-(benzoyloxy)-2-(methoxymethyl)tetrahydro-3-furanyl benzoate and (2R,3R,4R,5R)-5-(acetyloxy)-4-(benzoyloxy)-2-(methoxymethyl)tetrahydro-3-furanyl benzoate (preparation 4) (6 g, 14.5 mmol), ammonium sulfate (200 mg, 1.2 mmol), 1,1,1,3,3,3-hexamethyidisilazane (150 ml), bromotrimethylsilane (8 ml, 177 mmol), acetonitrile (80 ml), dichloromethane (80 ml) and bismuth tribromide (0.35 g, 0.24 mmol). The product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (99.5:0.5). This gave the title compound (7.9 g) as a white foam. MS: 619 (MH+).

Aufarbeitung

  1. customThe product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (99.5:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-d0161171eeee41c795f891434c6eb1cc
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326359B1

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