Trimethylsilyl triflate → 2-(Cyclopropylamino)-4,5,6-trichloro-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazole

HRID 1532596Notes

Reaction equation

HRID 1532596 reaction equation
[CH:1]1([NH:4][C:5]2[NH:9][C:8]3[CH:10]=[C:11]([Cl:16])[C:12]([Cl:15])=[C:13]([Cl:14])[C:7]=3[N:6]=2)[CH2:3][CH2:2]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:45]1[O:57][C@@H:56]([CH2:58][O:59][C:60](=[O:62])[CH3:61])[C@H:51]([O:52][C:53](=[O:55])[CH3:54])[C@@H:46]1[O:47][C:48](=[O:50])[CH3:49])(=O)C>ClCCCl>[CH:1]1([NH:4][C:5]2[N:9]([C@H:45]3[O:57][C@@H:56]([CH2:58][O:59][C:60](=[O:62])[CH3:61])[C@H:51]([O:52][C:53](=[O:55])[CH3:54])[C@@H:46]3[O:47][C:48](=[O:50])[CH3:49])[C:8]3[CH:10]=[C:11]([Cl:16])[C:12]([Cl:15])=[C:13]([Cl:14])[C:7]=3[N:6]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 65367Trimethylsilyl triflateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 114934341,2,3,5-tetra-O-acetyl-L-ribofuranoseHCID 229954112-(Cyclopropylamino)-4,5,6-trichloro-1H-benzimidazole

Product 1

HCID 213565052-(Cyclopropylamino)-4,5,6-trichloro-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazoleYield 52%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-(Cyclopropylamino)-4,5,6-trichloro-1H-benzimidazole (1.32 g, 4.00 mmol), N,O-bis(trimethylsilyl)acetamide (1.0 mL, 0.82 g, 4.05 mmol), trimethylsilyl trifluoromethanesulfonate (0.5 mL, 0.58 g, 2.59 mmol), 1,2,3,5-tetra-O-acetyl-L-ribofuranose (1.70 g, 5.34 mmol) and 1,2-dichloroethane (12 mL) were used according to general procedure II. The product was purified by silica gel chromatography using 60:1 dichloromethane/methanol to afford 1.11 g (52%) of a yellow foam. MS (CI): m/z 534 (M+1).

Workup

  1. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d66f655cbb4c4c86996029f8eac622b4
Source dataset
uspto-grants-2001_03
Patent number
US06204249B1

Reaction notes

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