반응 #351060

반응 방정식

Compound 64

2-Chloro-5,6-difluoro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)benzimidazole

→

65

2-Chloro-5,6-difluoro-1-(β-D-ribofuranosyl)benzimidazole

용매

NH3 MeOH

반응 조건

후처리

1. 1
   기타The reaction mixture was evaporated
2. 2
   기타to give a solid
3. 3
   기타This was recrystallized from MeOH

실험 절차

Compound 64 (0.894 g, 2 mmole) was treated with 20 mL of NH3 /MeOH in a pressure bottle at room temperature for 3 hr. The reaction mixture was evaporated and coevaporated with MeOH to give a solid. This was recrystallized from MeOH to give 0.573 g (3 crops, 89%) of 65 as a crystalline compound. MP ~215° C. (dec.); MS m/e 320.0385 (20%, M+ =320.0375); 1H NMR (DMSO-d6): d 8.34 (dd, 1, 7-H, 3JF-H =11.5 Hz, 4JF-H =7.5 Hz), 7.77 (dd, 1, 4-H, 3JF-H =11.0 Hz, JF-H =7.5 Hz), 5.88 (d, 1, 1'-H, J1'-2' =8.0 Hz), 5.50 (d, 1, 2'-OH, J2-2-OH =6.5 Hz), 5.45 (t, 1, 5'-OH, J5'-5'OH =4.5 Hz), 5.30 (d, 1, 3'-OH, J3'-3'OH =4.5 Hz), 4.40 (m, 1, 2'-H, J2'-3' =5.5 Hz), 4.14 (m, 1, 3'-H, J3'-4' =1.5 Hz), 4.01 (m, 1, 4'-H), 3.72 (m, 2, 5'-H, J5'-4' =2.5 Hz, J5'-5" =12.0 Hz); 13C NMR (DMSO-d6): d 148.53, 148.42, 148.37, 148.26, 145.88, 145.76, 145.72, 145.60 (C5 and C6, 1JF-C =241 Hz, 2JF-C =16 Hz), 140.84 (C2), 137.16, 137.04 (C3a, 3JF-C =11 Hz), 128.55, 128.42 (C7a, 3JF-C =12 Hz), 106.77, 106.54 (C4, 2JF-C =20 Hz), 102.12, 101.84 (C7, 2JF-C =25 Hz), 89.10 (C1'), 86.39 (C4'), 71.55 (C2'), 69.81 (C3'), 6.12 (C5').

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