반응 #351062

반응 방정식

72

2,5-Dichloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)benzimidazole

→

73

2,5-Dichloro-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 solid was recrystallized from MeOH

실험 절차

A solution of 0.226 g (0.508 mmole) of 72 in 10 mL of NH3 /MeOH was stirred in a pressure bottle at room temperature for 5 hr. The reaction mixture was evaporated and coevaporated with MeOH (3×) to give a solid. This solid was recrystallized from MeOH to give 0.136 g (76%, based on C12H12Cl2N2O4MeOH) of 73 as white crystals. MP 102°-150° C. (melted over a large range of temperature). MS (CI) m/e 319.0242 (37%, MH+ =319.0252). 1H NMR (DMSO-d6): d 8.06 (d, 1, 7-H, J7-6 =9.0 Hz), 7.73 (d, 1, 4-H, J4-6 =2.0 Hz), 7.30 (dd, 1, 6-H), 5.89 (d, 1, 1'-H, J1-2 =8.0 Hz), 5.51 (d, 1, 2'-OH, J2'-2'OH =65 Hz), 5.29 (d, 1, 3'-OH J3'-3'OH =4.5 Hz),5.26 (t, 1, 5'-OH, J5'-5'OH =5-0 Hz), 4.45 (m, 1, 2'-H, J2'-3' =5.5 Hz), 4.12 (m, 1, 3'-H, J3'-4' =2.0 Hz), 3.99 (m, 1, 4'-H, J4'-5' =J4'-5" =3.5 Hz), 3.69 (m, 2, 5'-H and 5"-H, J5'-5" =12.0 Hz). 13C NMR (DMSO-d6) d 142.36 (C3a), 141.40 (C2), 131.88 (C7a), 127.49 (C5), 123.32 (C6), 118.40 (C4), 114.51 (C7), 89.07 (C1'), 86.23 (C4'), 71.49 (C2'), 69.75 (C3'), 61.23 (C5').

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