Nitromethane → 1-Methyl-3-[2-(2-nitrophenyl)propoxycarbonyl]imidazolium triflate

HRID 354212Notes

Reaction equation

C1N=CN([C:6]([N:8]2[CH:12]=[N:11][CH:10]=[CH:9]2)=[O:7])C=1.[N+]([CH3:16])([O-])=O.C[O:18][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20].[N+:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH:35]([CH3:38])[CH2:36][OH:37])([O-:28])=[O:27]>ClCCl>[O-:21][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:20])=[O:18].[CH3:16][N+:11]1[CH:10]=[CH:9][N:8]([C:6]([O:37][CH2:36][CH:35]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N+:26]([O-:28])=[O:27])[CH3:38])=[O:7])[CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2.19 g N,N-carbonyldiimidazole (13.5 mmol) are dissolved in 40 ml absolute dichloromethane and 10 ml absolute nitromethane in a nitrogen atmosphere and cooled to 0° C. 3 ml trifluoromethanesulfonic acid methyl ester (27 mmol) are added and stirred at 0° C. After 30 minutes, a solution consisting of 1.22 g 2-(2-nitrophenyl)propanol (6.75 mmol) in 10 ml absolute dichloromethane are added. After a reaction time of 1 hour, the reaction solution can be used directly for acylation with 1.2 equivalents of the 5′-O-protected nucleoside building blocks.

Workup

additionare added
customAfter a reaction time of 1 hour

Sources & evidence

ORD record: ord-7f2e1a0c334b4e448e18c59b1dd654ca
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06756492B1

Reaction notes

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