تفاعل #1951033

معادلة التفاعل

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

sodium methoxide

→

4.48

المردود 56.3%

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

المردود 56.3%

المذيبات

MeOH CHCl3

MeOH

MeOH CHCl3

ظروف التفاعل

المعالجة

1. 1
   أخرىthe solvent was removed under vacuum
2. 2
   استخلاصwater (5 mL), and the suspension extracted with EtOAc (2×50 mL)
3. 3
   تجفيفThe combined organic extracts were dried over MgSO4
4. 4
   ترشيحfiltered
5. 5
   أخرىevaporated
6. 6
   أخرىto yield a yellow-orange solid
7. 7
   workup.ADDITIONFractions containing product
8. 8
   أخرىevaporated
9. 9
   أخرىto yield a white solid which
10. 10
    أخرىwas recrystallized from MeOH/H2O

الإجراء التجريبي

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.

المصدر