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

HRID 727021Notes

Reaction equation

HRID 727021 reaction equation
[Cl:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][O:21]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@H:8]2[O:9]C(=O)C)[C:5]2[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:4]=2[N:3]=1>N.CO>[Cl:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@H:8]2[OH:9])[C:5]2[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:4]=2[N:3]=1

Participants

3

Reactant 1

HCID 106232802-Chloro-5,6-difluoro-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)benzimidazole

Product 1

HCID 4694232-Chloro-5,6-difluoro-1-(beta-D-ribofuranosyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

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, 1 JF-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').

Workup

  1. customThe reaction mixture was evaporated
  2. customto give a solid
  3. customThis was recrystallized from MeOH

Sources & evidence

ORD record
ord-80ef6bbc34ff49308dc675318008be89
Source dataset
uspto-grants-1998_01
Patent number
US05712255

Reaction notes

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