反応 #1951033

反応方程式

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

sodium methoxide

→

4.48

収率 56.3%

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

収率 56.3%

溶媒

MeOH CHCl3

MeOH

MeOH CHCl3

反応条件

後処理

1. 1
   その他the solvent was removed under vacuum
2. 2
   抽出water (5 mL), and the suspension extracted with EtOAc (2×50 mL)
3. 3
   乾燥The combined organic extracts were dried over MgSO4
4. 4
   ろ過filtered
5. 5
   その他evaporated
6. 6
   その他to yield a yellow-orange solid
7. 7
   workup.ADDITIONFractions containing product
8. 8
   その他evaporated
9. 9
   その他to yield a white solid which
10. 10
    その他was recrystallized from MeOH/H2O

実験手順

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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