Trimethylsilyl triflate → 4-Chloro-2-(isopropylamino)-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazole

HRID 1167087Notes

Reaction equation

HRID 1167087 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][CH:12]([CH3:14])[CH3:13])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(O[CH:43]1[O:55][C@@H:54]([CH2:56][O:57][C:58](=[O:60])[CH3:59])[C@H:49]([O:50][C:51](=[O:53])[CH3:52])[C@@H:44]1[O:45][C:46](=[O:48])[CH3:47])(=O)C>ClCCCl>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][CH:12]([CH3:14])[CH3:13])[N:7]([C@H:43]3[O:55][C@@H:54]([CH2:56][O:57][C:58](=[O:60])[CH3:59])[C@H:49]([O:50][C:51](=[O:53])[CH3:52])[C@@H:44]3[O:45][C:46](=[O:48])[CH3:47])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 65367Trimethylsilyl triflateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 114934341,2,3,5-tetra-O-acetyl-L-ribofuranoseHCID 229954304-Chloro-2-(isopropylamino)-1H-benzimidazole

Product 1

HCID 572936104-Chloro-2-(isopropylamino)-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazoleYield 47%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-Chloro-2-(isopropylamino)-1H-benzimidazole (2.24 g, 10.68 mmol), N,O-bis(trimethylsilyl)acetamide (3.00 mL, 2.47g, 12.14 mmol), trimethylsilyl trifluoromethanesulfonate (1.2 mL, 1.42 g, 6.00 mmol), 1,2,3,5-tetra-O-acetyl-L-ribofuranose (4.46 g, 14.01 mmol) and 1,2-dichloroethane (35 mL) were used according to general procedure II. The product was purified by silica gel chromatography using 95:5 dichloromethane/acetonitrile to afford 2.34 g (47%) of an off-white foam MS (EI): m/z 468.2 (M+H).

Workup

  1. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ba0246d372474224a92a67a4ef7434be
Source dataset
uspto-grants-2003_09
Patent number
US06617315B1

Reaction notes

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