Reaktion #806268

Reaktionsgleichung

2-(6-cyano-1-hexyn-1-yl)adenosine

triethyl phosphate

phosphorous oxychloride

sodium hydroxide

→

triethylammonium 2-(6-cyano-1-hexyn-1-yl)adenosine 5′-monophosphate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Waschenthe resultant mixture was washed with ether
3. 3
   SonstigeThe aqueous layer was separated
4. 4
   Sonstigewater was removed under reduced pressure
5. 5
   Sonstigethe residue was purified by C18 silica gel column chromatography (0.1M triethylammonium acetate buffer:acetonitrile=100:0 to 60:40)
6. 6
   EinengenThe thus-obtained fraction was concentrated
7. 7
   Sonstigeto thereby remove the triethylammonium acetate buffer
8. 8
   SonstigeThe residue was freeze-dried

Vorschrift

Under argon, A 2-(6-cyano-1-hexyn-1-yl)adenosine (2.41 g) was dissolved in triethyl phosphate (15 mL), and, under ice-cooling conditions, phosphorous oxychloride (25.2 mL, 3.9 eq.) was added thereto, followed by stirring at the same temperature for 5 hours. The reaction mixture was added dropwise to a 10% sodium hydroxide solution (300 mL), and the resultant mixture was washed with ether. The aqueous layer was separated and water was removed under reduced pressure, and the residue was purified by C18 silica gel column chromatography (0.1M triethylammonium acetate buffer:acetonitrile=100:0 to 60:40). The thus-obtained fraction was concentrated, and the concentrate was subjected to C18 silica gel column chromatography (water:acetonitrile=100:0 to 60:40), to thereby remove the triethylammonium acetate buffer. The residue was freeze-dried, to thereby yield 1.14 g of the above-titled compound as a colorless amorphous substance.

Quelle