반응 #1951037

반응 방정식

5,6-Dichloro-2-bromo-3-formyl-1-(5-O-acetyl-β-D-ribofuranosyl)indole

sodium methoxide

MeOH H2O

→

4.137

수율 47.0%

5,6-Dichloro-2-bromo-3-formyl-1-(β-D-ribofuranosyl)indole

수율 47.0%

용매

MeOH

MeOH

반응 조건

후처리

1. 1
   기타was consumed (TLC)
2. 2
   workup.ADDITIONWater (30 mL) was added
3. 3
   기타the solution evaporated until the MeOH
4. 4
   기타was completely removed
5. 5
   추출The residual aqueous suspension was extracted with EtOAc (3×30 mL)
6. 6
   세척the combined organic extracts washed with brine (20 mL)
7. 7
   건조dried over MgSO4
8. 8
   여과filtered
9. 9
   기타evaporated
10. 10
    기타to yield a white solid
11. 11
    workup.ADDITIONFractions containing product
12. 12
    기타evaporated
13. 13
    기타to yield a white solid which
14. 14
    기타was recrystallized from MeOH and H2O

실험 절차

5,6-Dichloro-2-bromo-3-formyl-1-(5-O-acetyl-β-D-ribofuranosyl)indole (4.136, 101 mg, 0.22 mmol) was dissolved in dry MeOH (10 mL) to which was added sodium methoxide (25 mg, 0.46 mmol). The solution was stirred at room temperature for 15 min, until the starting material was consumed (TLC). Water (30 mL) was added and the solution evaporated until the MeOH was completely removed. The residual aqueous suspension was extracted with EtOAc (3×30 mL) and the combined organic extracts washed with brine (20 mL), dried over MgSO4, filtered and evaporated to yield a white solid. The solid was dissolved in MeOH (1 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 a white solid which was recrystallized from MeOH and H2O to yield 43 mg (47%) of 4.137 as a pale tan powder: mp 210-211° C.; Rf0.2 (10% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 9.95 (s, 1H), 8.69 (s, 1H), 8.28 (s, 1H), 6.06 (d, 1H), 5.49-5.43 (m, 2H, D2O exch.), 5.31 (d, 1H, D2O exch.), 4.44 (q, 1H), 4.18 (m, 1H), 4.04 (d, 1H), 3.77-3.71 (m, 2H). 13C-NMR (125 MHz, DMSO-d6): δ 185.53, 134.05, 128.85, 126.58, 126.47, 125.31, 120.56, 116.00, 114.68, 90.27, 86.55, 71.69, 69.62, 60.98. HRMS (EI) m/z calcd. for C14H12BrCl2NO5 422.9276, found 422.9271. Anal calcd for C14H12BrCl2NO5: C, 39.56; H, 2.85; N, 3.30. Found: C, 39.77; H, 3.03; N, 3.32.

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