Реакция #1951033

Уравнение реакции

2,5,6-Trichloro-3-trifluoroacetyl-1-(5-O-acetyl-β-D-ribofuranosyl)indole

sodium methoxide

→

4.48

Выход 56.3%

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

Выход 56.3%

Растворители

MeOH CHCl3

MeOH

MeOH CHCl3

Условия реакции

Обработка

1. 1
   Другоеthe solvent was removed under vacuum
2. 2
   Экстракцияwater (5 mL), and the suspension extracted with EtOAc (2×50 mL)
3. 3
   СушкаThe combined organic extracts were dried over MgSO4
4. 4
   Фильтрацияfiltered
5. 5
   Другоеevaporated
6. 6
   Другоеto yield a yellow-orange solid
7. 7
   workup.ADDITIONFractions containing product
8. 8
   Другоеevaporated
9. 9
   Другоеto yield a white solid which
10. 10
    Другоеwas recrystallized from MeOH/H2O

Методика

2,5,6-Trichloro-3-trifluoroacetyl-1-(5-O-acetyl-β-D-ribofuranosyl)indole (4.45, 94 mg, 0.19 mmol) was dissolved in dry MeOH (20 mL) to which was added sodium methoxide (12 mg, 0.22 mmol). The solution was stirred at room temperature for 90 min, then the solvent was removed under vacuum. The residue was suspended in brine (40 mL) and water (5 mL), and the suspension extracted with EtOAc (2×50 mL). The combined organic extracts were dried over MgSO4, filtered and evaporated to yield a yellow-orange solid. The solid was dissolved in 10% MeOH/CHCl3 (1 mL) and subjected to column chromatography (40×350 mm) on silica gel with 10% MeOH/CHCl3. Fractions containing product were pooled and evaporated to yield a white solid which was recrystallized from MeOH/H2O to yield 48 mg (56%) of 4.48 as a pale yellow powder: mp 179-180 C; Rf0.3 (10% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 8.80 (s, 1H), 8.23 (s, 1H), 6.14 (d, 1H), 5.50 (b, 2H, D2O exch.), 5.34 (b, 1H, D2O exch.), 4.44 (t, 1H), 4.19 (dd, 1H), 4.06 (d, 1H), 3.76 (dq, 2H). 13C-NMR (125 MHz, DMSO-d6): δ 173.47 (J=37 Hz), 132.34, 132.65, 127.38, 127.28, 125.47, 121.35, 116.29, 115.88 (J=289 Hz), 106.90, 89.42, 86.88, 71.96, 69.49, 60.86. 19F-NMR (300 MHz, DMSO-d6): δ −72.34. HRMS (EI) m/z calcd. for C15H11Cl3F3NO5 446.9655, found 446.9661. Anal calcd for C15H11Cl3F3NO5: C, 40.16; H, 2.47; N, 3.12. Found: C, 40.18; H, 2.60; N, 2.98.

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