2,4,6-Trimethylpyridine → (4R)-N-[(1S)-1-Methyl-2-nitroxyethyl]-2-oxothiazolidin-4-yl-carboxamide

HRID 442759

Reaction equation

HRID 442759 reaction equation
[B-](F)(F)(F)F.[N+:6](=[O:8])=[O:7].N1C(C)=CC(C)=CC=1C.[CH3:18][C@H:19]([NH:22][C:23]([C@@H:25]1[CH2:29][S:28][C:27](=[O:30])[NH:26]1)=[O:24])[CH2:20][OH:21]>C(#N)C>[CH3:18][C@H:19]([NH:22][C:23]([C@@H:25]1[CH2:29][S:28][C:27](=[O:30])[NH:26]1)=[O:24])[CH2:20][O:21][N+:6]([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 11073463Nitronium tetrafluoroborateHCID 21309140(4R)-N-[(1S)-1-Methyl-2-hydroxyethyl]-2-oxothiazolidin-4-yl-carboxamide

Product 1

HCID 9816362(4R)-N-[(1S)-1-Methyl-2-nitroxyethyl]-2-oxothiazolidin-4-yl-carboxamideYield 29.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 10 ml of dry acetonitrile were dissolved 478 mg of nitronium tetrafluoroboron (85% content), 0.43 ml of 2,4,6-collidine was added thereto with stirring under ice-cooling, and the mixture was stirred under ice-cooling for 30 minutes. To the resulting mixture were added 500 mg of (4R)-N-[(1S)-1-methyl-2-hydroxyethyl]-2-oxothiazolidin-4-yl-carboxamide, and the mixture was stirred at room temperature for 1 hour and 45 minutes. Then, the solvent was distilled off under reduced pressure and the thus obtained residue was purified by silica gel column chromatography employing cyclohexane-ethyl acetate (3:7) as an eluent to obtain 178 mg of the desired compound as colorless crystals.

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooling for 30 minutes
  5. stirringthe mixture was stirred at room temperature for 1 hour and 45 minutes
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customthe thus obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e09145e95582489a842ab3d05043dfe5
Source dataset
uspto-grants-1999_04
Patent number
US05891898

Linked notes

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