2,4,6-Trimethylpyridine → HCID 88212429, compound

HRID 582593Notes

Reaction equation

HRID 582593 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](=[S:41])[C@H:24]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:20][OH:21]>C(#N)C>[CH3:18][C@H:19]([NH:22][C:23](=[S:41])[C@H:24]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:20][O:21][N+:6]([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 11073463Nitronium tetrafluoroborateHCID 88212053HCID 88212053, compound

Product 1

HCID 88212429HCID 88212429, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

In 25 ml of dry acetonitrile were dissolved 1.24 g of nitronium tetrafluoroboron (85% content), 1.12 g of 2,4,6-collidine was added thereto with stirring under ice-cooling, and the mixture was stirred under ice-cooling for 30 minutes. Then, a solution obtained by dissolving 2.5 g of N-[(1S)-1-methyl-2-hydroxyethyl]-(2R)-2-t-butoxycarbonylamino-3-t-butoxycarbonylthiopropanamide in 25 ml of dry acetonitrile was added to the mixture and the resulting mixture was stirred at room temperature for 3 hours. 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 (4:1) as an eluent to obtain 1.39 g of the desired compound as pale yellow crystals.

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooling for 30 minutes
  5. customThen, a solution obtained
  6. additionwas added to the mixture
  7. stirringthe resulting mixture was stirred at room temperature for 3 hours
  8. distillationThen, the solvent was distilled off under reduced pressure
  9. customthe thus obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ddf18e199ce64e8fa3100f8e80ffc5f5
Source dataset
uspto-grants-1999_07
Patent number
US05925658

Reaction notes

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