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

HRID 1532610

Reaction equation

HRID 1532610 reaction equation
[Cl:1][N:2]1[C:6]2[C:7]([Cl:11])=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][CH:3]1[NH:12][CH:13]([CH3:15])[CH3:14].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[C@H:44]1[O:56][C@@H:55]([CH2:57][O:58][C:59](=[O:61])[CH3:60])[C@H:50]([O:51][C:52](=[O:54])[CH3:53])[C@@H:45]1[O:46][C:47](=[O:49])[CH3:48])(=O)C>ClCCCl>[Cl:1][N:2]1[C:6]2[C:7]([Cl:11])=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([C@H:44]2[O:56][C@@H:55]([CH2:57][O:58][C:59](=[O:61])[CH3:60])[C@H:50]([O:51][C:52](=[O:54])[CH3:53])[C@@H:45]2[O:46][C:47](=[O:49])[CH3:48])[CH:3]1[NH:12][CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 65367Trimethylsilyl triflateHCID 908100(2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 229954523,4-Dichloro-2-(isopropylamino)-1H-benzimidazole

Product 1

HCID 572228243,4-Dichloro-2-(isopropylamino)-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazoleYield 56.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3,4-Dichloro-2-(isopropylamino)-1H-benzimidazole (2.01 g, 7.31 mmol), N,O-bis(trimethylsilyl)acetamide (2.0 mL, 1.65 g, 8.09 mmol), trimethylsilyl trifluoromethanesulfonate (0.9 mL, 1.06 g, 4.50 mmol), 1,2,3,5-tetra-O-acetyl-beta-L-ribofuranose (3.03 g, 9.52 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 2.08 g (56%) of a yellow foam. MS (EI): m/z 502.0 (M+H).

Workup

  1. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-47c9aae3f01b4bacb0f586b21ab22539
Source dataset
uspto-grants-2001_03
Patent number
US06204249B1

Linked notes

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