Trimethylsilyl triflate → HCID 137010181, Verbindung

HRID 2205177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2205177
[O:1]=[C:2]1[NH:10][C:9]([NH:11][C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[N:8][C:7]2[NH:6][CH:5]=[N:4][C:3]1=2.C(O[CH:21]1[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:24]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@:23]([CH2:41][O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([CH:38]([F:40])[F:39])[O:22]1)(=O)C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.C([O-])(O)=O.[Na+]>CC#N>[C:27]([O:26][C@@H:25]1[C@H:24]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@:23]([CH2:41][O:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)([CH:38]([F:39])[F:40])[O:22][C@H:21]1[N:6]1[CH:5]=[N:4][C:3]2[C:2](=[O:1])[NH:10][C:9]([NH:11][C:12](=[O:16])[CH:13]([CH3:14])[CH3:15])=[N:8][C:7]1=2)(=[O:29])[CH3:28]

Komponenten

6

Edukt 4

HCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 131735802HCID 131735802, VerbindungHCID 178454493HCID 178454493, Verbindung

Produkt 1

HCID 137010181HCID 137010181, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of compound N-(6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide (0.57 g, 2.58 mmol) in anhydrous CH3CN (50 mL) was added BSA (1.26 mL, 5.17 mmol) portion-wise while maintaining the reaction temperature at 25° C. Then the reaction was stirred at 40° C. for 1 h until a clear solution persisted. Compound 5 (0.6 g, 1.29 mmol) in CH3CN (5 mL) was added into the mixture at 0° C. followed by TMSOTf (0.94 mL, 5.17 mmol). The mixture was stirred at 40° C. for 2 h and then poured into saturated NaHCO3 solution (10 mL) at 0° C., extracted with ethyl acetate, washed with water, brine solution, dried over Na2SO4 and evaporated to dryness under reduced pressure. The crude compound was purified by silica gel chromatography [petroleum ether:ethyl acetate (5:1 to 1:1)] to provide the product 21 as a white foam (0.5 g, 60%). LC-MS: (M+H)+=626

Aufarbeitung

  1. stirringThe mixture was stirred at 40° C. for 2 h
  2. extractionextracted with ethyl acetate
  3. washwashed with water, brine solution
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness under reduced pressure
  6. customThe crude compound was purified by silica gel chromatography [petroleum ether:ethyl acetate (5:1 to 1:1)]

Quellen und Nachweise

ORD-Eintrag
ord-372499770dc44153b91264f3c6e14510
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09370569B2

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