반응 #1951027

반응 방정식

2,5,6-Trichloro-3-cyano-1-(β-D-ribofuranosyl)indole

MeOH H2O

→

4.34

수율 58.0%

Methyl 2,5,6-Trichloro-1-(β-D-ribofuranosyl)indole-3-formimidate

수율 58.0%

용매

DMF

MeOH

반응 조건

후처리

1. 1
   온도was cooled to 0 C in an ice bath
2. 2
   기타Hydrogen chloride gas was slowly bubbled through the solution for 2 h
3. 3
   기타the reaction vessel was tightly capped
4. 4
   workup.ADDITIONThe acidic solution was diluted with Et2O (20 mL)
5. 5
   기타evaporated to dryness
6. 6
   추출extracted with EtOAc (3×100 mL, with vigorous shaking)
7. 7
   건조The combined organic extracts were dried over MgSO4
8. 8
   여과filtered
9. 9
   기타evaporated
10. 10
    기타to yield a white solid which
11. 11
    workup.ADDITIONFractions containing product
12. 12
    기타evaporated

실험 절차

2,5,6-Trichloro-3-cyano-1-(β-D-ribofuranosyl)indole (4.4, 107 mg, 0.28 mmol) was dissolved in dry MeOH (10 mL) which was cooled to 0 C in an ice bath. Hydrogen chloride gas was slowly bubbled through the solution for 2 h, then the reaction vessel was tightly capped, and the resulting solution was stirred at room temperature for 24 h. The acidic solution was diluted with Et2O (20 mL) and evaporated to dryness. The residual solid was suspended in 10% aqueous NaHCO3 (100 mL) and extracted with EtOAc (3×100 mL, with vigorous shaking). The combined organic extracts were dried over MgSO4, filtered and evaporated to yield a white solid which was dissolved in DMF (0.5 mL) and subjected to column chromatography (40×350 mm) on C18-reverse phase silica gel with 75% MeOH/H2O. Fractions containing product were pooled and evaporated to yield 64 mg (58%) of 4.34 as a white crystalline solid: mp 248-249 C; Rf0.6 (20% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 8.55 (s, 1H), 8.43 (s, 1H, D2O exch.), 7.96 (s, 1H), 5.98 (d, 1H), 5.39 (d, 1H, D2O exch.), 5.37 (t, 1H, D2O exch.), 5.24 (d, 1H, D2O exch.), 4.41 (q, 1H), 4.14 (s, 1H), 3.98 (d, 1H), 3.85 (s, 3H), 3.71 (m, 2H). 13C-NMR (125 MHz, DMSO-d6): δ 161.40, 132.01, 128.23, 125.67, 124.82, 124.50, 121.32, 115.19, 106.29, 88.73, 86.08, 71.40, 69.50, 60.99, 52.45. HRMS (EI) m/z calcd. for C15H15Cl3N2O5 408.0047, found 408.0043. Anal calcd for C15H15Cl3N2O5: C, 43.98; H, 3.69; N, 6.84. Found: C, 43.97; H, 3.81; N, 6.75.

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