반응 #47764

반응 방정식

NaHCO3

Phosphorus oxychloride

16

5-Acetylamino-3-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidine-2,7-dione

triethylamine

→

81

수율 90.0%

5-Acetylamino-7-chloro-3-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2-one

수율 90.0%

용매

chloroform

반응 조건

후처리

1. 1
   온도The mixture was cooled to ambient temperature
2. 2
   기타The layers were separated
3. 3
   추출aqueous layer back extracted with methylene chloride (2×100 mL)
4. 4
   건조were dried (MgSO4)
5. 5
   여과filtered
6. 6
   농축concentrated to a yellow solid
7. 7
   기타Purification

실험 절차

Phosphorus oxychloride (6.42 mL, 70.2 mmol) was added dropwise to a solution of 16 (3.40 g, 7.02 mmol), triethylamine (1.96 mL, 14.04 mmol), and chloroform (14 mL) over 30 minutes at room temperature under nitrogen. The reaction mixture was then heated to 70° C. for 30 h. The mixture was cooled to ambient temperature, added dropwise over 2 h to a 0° C. solution of saturated aq. NaHCO3 (500 mL), and stirred for an additional 1 h. The layers were separated, aqueous layer back extracted with methylene chloride (2×100 mL), combined organic layers were dried (MgSO4), filtered and concentrated to a yellow solid. Purification was achieved via flash chromatography (SiO2, 5% Acetone-CHCl3) to afford 81 (3.17 g, 90%) as a white solid: 1H NMR (400 MHz, d6-DMSO) δ 11.08 (s, 1H), 6.09 (d, J=4.0 Hz, 1H), 5.99 (dd, J=6.0, 4.0 Hz, 1H), 5.76 (t, J=6.8 Hz, 1H), 4.41 (dd, J=11.2, 3.2 Hz, 1H), 4.32 (td, J=7.2, 3.2 Hz, 1H), 4.24 (dd, J=11.6, 6.8 Hz, 1H), 2.18 (s, 3H), 2.12 (s, 3H), 2.11 (s, 3H), 2.03 (s, 3H); [M+H]+ 503.3.

출처