Tert-Butyl nitrite → Adenosine,2-bromo-2'-deoxy-(9CI)

HRID 1358696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1358696
[CH:1]1[N:9]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])O[CH2:11]2)[C:8]2[N:7]=[C:6](N)[N:5]=[C:4]([NH2:18])[C:3]=2[N:2]=1.[Sb](Br)(Br)[Br:20].N([O:25][C:26](C)(C)C)=O.C(#N)C.O>ClC(Cl)C.CS(C)=O.C(O)(=O)C>[Br:20][C:6]1[N:5]=[C:4]([NH2:18])[C:3]2[N:2]=[CH:1][N:9]([C:8]=2[N:7]=1)[C@@H:10]1[O:14][C@H:13]([CH2:15][OH:16])[C@@H:26]([OH:25])[CH2:11]1

Komponenten

7

Edukt 4

HCID 10906Tert-Butyl nitriteHCID 24615Antimony tribromideHCID 124088AmdoxovirHCID 18373917Acetonitrile--water (1/1)

Produkt 1

HCID 10065192Adenosine,2-bromo-2'-deoxy-(9CI)

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 20230201dichloroethane DMSOLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

DAPD (2 g, 7.5 mmol) was suspended in 170 mL dichloroethane/DMSO (4:1) and cooled to 0° C. under an inert atmosphere. To this was added antimony tribromide (3.8 g, 10.5 mmol) and tert-butyl nitrite (1.85 mL, 1.6 g, 15.5 mmol) followed by stirring while allowing the reaction to warm to room temperature. Analysis by HPLC [Novapak C-18; 5% acetonitrile/water, 0.1M TEA, pH 7 with acetic acid] revealed a new peak that eluted at 5.59 minutes (a retention time that was expected for the brominated product) with concomitant loss of DAPD starting material. The reaction was stirred overnight and quenched with triethylamine. The conversion by HPLC was 26% indicating the synthesis of 2-bromo-2′-deoxyadenosine.

Aufarbeitung

  1. customthe reaction
  2. temperatureto warm to room temperature
  3. washthat eluted at 5.59 minutes (a retention time that
  4. stirringThe reaction was stirred overnight
  5. customquenched with triethylamine
  6. customthe synthesis of 2-bromo-2′-deoxyadenosine

Quellen und Nachweise

ORD-Eintrag
ord-68c5885cd720466eba66ef062d0fd6aa
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596858B2

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