Water → 2,2-Dimethyl-propionic acid 8-(4-acetylamino-benzyl)-3-butyl-1-[2-(tert-butyl-dimethyl-silanyloxy)-benzyl]-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester

HRID 720628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 720628
[C:1]([NH:4][C:5]1[CH:34]=[CH:33][C:8]([CH2:9][C:10]2[N:18]([CH2:19][O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C:17]3[C:16](=[O:27])[NH:15][C:14](=[O:28])[N:13]([CH2:29][CH2:30][CH2:31][CH3:32])[C:12]=3[N:11]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:42][C:43]1[CH:56]=[CH:55][CH:54]=[CH:53][C:44]=1[O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47].O>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>[C:1]([NH:4][C:5]1[CH:34]=[CH:33][C:8]([CH2:9][C:10]2[N:18]([CH2:19][O:20][C:21](=[O:26])[C:22]([CH3:24])([CH3:25])[CH3:23])[C:17]3[C:16](=[O:27])[N:15]([CH2:42][C:43]4[CH:56]=[CH:55][CH:54]=[CH:53][C:44]=4[O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[C:14](=[O:28])[N:13]([CH2:29][CH2:30][CH2:31][CH3:32])[C:12]=3[N:11]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 13594450[2-(Bromomethyl)phenoxy](tert-butyl)dimethylsilaneHCID 587392662,2-Dimethyl-propionic acid 8-(4-acetylamino-benzyl)-3-butyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester

Produkt 1

HCID 688632082,2-Dimethyl-propionic acid 8-(4-acetylamino-benzyl)-3-butyl-1-[2-(tert-butyl-dimethyl-silanyloxy)-benzyl]-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl esterAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 2,2-dimethyl-propionic acid 8-(4-acetylamino-benzyl)-3-butyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester (100 mg, 0.21 mmol) in N,N-dimethylformamide (2.0 mL) was treated with sodium carbonate (68 mg, 0.64 mmol), (2-bromomethyl-phenoxy)-tert-butyl-dimethyl-silane (70.6 mg, 0.23 mmol) in N,N-dimethylformamide (0.5 mL), and tetrabutylammonium iodide (24 mg, 0.06 mmol). The reaction was heated at 50° C. for 4 h. At this time, the reaction was poured onto a solution of water (125 mL) and a IN aqueous hydrochloric acid solution (1.28 mL). The product was extracted into ethyl acetate. The organics were washed with water (1×100 mL) and a saturated aqueous sodium chloride solution (1×100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 1:4 ethyl acetate/petroleum ether) afforded 2,2-dimethyl-propionic acid 8-(4-acetylamino-benzyl)-3-butyl-1-[2-(tert-butyl-dimethyl-silanyloxy)-benzyl]-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester (91.9 mg, 63%) as an off-white foam: FAB-HRMS m/e calcd for C37H51N5O6Si (M+H)+ 690.3687, found 690.3685.

Aufarbeitung

  1. extractionThe product was extracted into ethyl acetate
  2. washThe organics were washed with water (1×100 mL)
  3. dry with materiala saturated aqueous sodium chloride solution (1×100 mL), dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-65e939033ea24b2594ebf21da0cca6c7
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135475B2

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