تفاعل #1951032

معادلة التفاعل

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

sodium methoxide

→

4.47

المردود 198.1%

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

المردود 198.1%

المذيبات

MeOH CHCl3

MeOH

MeOH CHCl3

ظروف التفاعل

المعالجة

1. 1
   أخرىthe solvent was then 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 white solid
7. 7
   workup.ADDITIONFractions containing product
8. 8
   أخرىevaporated
9. 9
   أخرىto yield a white solid which
10. 10
    أخرىwas recrystallized

الإجراء التجريبي

2,5,6-Trichloro-3-propionyl-1-(5-O-acetyl-β-D-ribofuranosyl)indole (4.44, 90 mg, 0.21 mmol) was dissolved in dry MeOH (15 mL) to which was added sodium methoxide (14 mg, 0.26 mmol). The solution was stirred at room temperature for 40 min, and the solvent was then removed under vacuum. The residue was suspended in brine (50 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 white 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 boiling EtOAc to yield 170 mg (81%) of 4.47 as a white crystalline solid: mp 239-240 C; Rf0.3 (10% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 8.63 (s, 1H), 8.44 (s, 1H), 6.06 (d, 1H), 5.44-5.41 (m, 2H, D2O exch.), 5.29 (d, 1H, D2O exch.), 4.42 (q, 1H), 4.17 (s, 1H), 3.74 (m, 2H), 3.04 (dd, 2H), 1.12 (t, 3H). 13C-NMR (125 MHz, DMSO-d6): δ 195.17, 132.45, 132.41, 126.13, 125.91, 125.84, 122.09, 115.39, 112.60, 88.90, 86.36, 71.58, 69.54, 60.97, 35.05, 7.98. HRMS (EI) m/z calcd. for C16H16Cl3NO5 407.0094, found 407.0089. Anal calcd for C16H16Cl3NO5: C, 47.02; H, 3.95; N, 3.43. Found: C, 46.85; H, 3.96; N, 3.47.

المصدر