반응 #806268

반응 방정식

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

반응 조건

후처리

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

실험 절차

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.

출처