Trifluoroacetic acid → HCID 66988452, compound

HRID 540398Notes

Reaction equation

HRID 540398 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[I-].[CH3:9][O:10][C:11]([CH2:13][CH2:14][C:15]1[N+:19]([CH3:20])=[CH:18][N:17](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:16]=1)=[O:12]>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:20][N:19]1[C:15]([CH2:14][CH2:13][C:11]([O:10][CH3:9])=[O:12])=[CH:16][N:17]=[CH:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178500008HCID 178500008, compound

Product 1

HCID 66988452HCID 66988452, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.5 ml of trifluoroacetic acid is added to a solution of 200 mg (0.37 mmol) of 5-(2-methoxycarbonylethyl)-1-methyl-3-trityl-3H-imidazol-1-ium iodide in 2 ml of dichloromethane. The reaction medium is left to stir overnight at ambient temperature and the solvents are evaporated off. The residue is purified by silica chromatography (eluent 9/1 DCM/MeOH. 80 mg of methyl 3-(3-methyl-3H-imidazol-4-yl)propionate trifluoroacetate are obtained with a yield of 76%.

Workup

  1. waitThe reaction medium is left
  2. customthe solvents are evaporated off
  3. customThe residue is purified by silica chromatography (eluent 9/1 DCM/MeOH

Sources & evidence

ORD record
ord-e302dbf731684548a8148b4716f36e8d
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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