反応 #806268

反応方程式

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

反応条件

後処理

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

実験手順

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.

出典