Acetic Acid → HCID 10766040, compound

HRID 1489418Notes

Reaction equation

HRID 1489418 reaction equation
[F:1][C:2]([F:20])([CH:17]([F:19])[F:18])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][NH:13][C:12]2=[O:16])=[CH:7][CH:6]=1.FC(F)(F)S(O[C@@H:27]([CH3:38])[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])(=O)=O.C(O)(=O)C>CN1CCCC1=O.[H-].[Na+].O1CCCC1.C(OCC)(=O)C>[F:20][C:2]([F:1])([CH:17]([F:19])[F:18])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][N:13]([C@H:27]([CH3:38])[C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])[C:12]2=[O:16])=[CH:7][CH:6]=1

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 10493689HCID 10493689, compoundHCID 10881508Phenylmethyl (2S)-2-[[(trifluoromethyl)sulfonyl]oxy]propanoate

Product 1

HCID 10766040HCID 10766040, compoundYield 85%

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 24758Sodium hydrideSolvent

Procedure

1-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone (4 g) was dissolved in 30 ml of 1-methyl-2-pyrrolidone, to which 60% sodium hydride in oil (0.55 g) was added. The mixture was vigorously stirred at room temperature for 30 minutes and then added to a solution of 5.2 g of benzyl (2S)-2-trifluoromethanesulfonyloxypropionate (prepared in Example 3) in 80 ml of tetrahydrofuran under nitrogen atmosphere at -40° to -50° C. over the period of 10 minutes. The mixture was stirred at -20° to -40° C. for 50 minutes, followed by addition of 9.6 ml of acetic acid. Then, the reaction solution was diluted with 100 ml of ethyl acetate, washed with 50 ml of water, 1N-hydrochloric acid (50 ml×2) and 50 ml of an aqueous solution of sodium chloride successively, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (silica gel: 200 g, eluent; hexane:ethyl acetate=2:3) to give 5.3 g of benzyl (2R)-2-[3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2,3-dihydro-2-oxo-1H-imidazol-1-yl]propionate (yield: 85%) as colorless powdery crystals.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at -20° to -40° C. for 50 minutes
  3. washwashed with 50 ml of water, 1N-hydrochloric acid (50 ml×2) and 50 ml of an aqueous solution of sodium chloride successively
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel chromatography (silica gel: 200 g, eluent; hexane:ethyl acetate=2:3)

Sources & evidence

ORD record
ord-e9edfe51366a444db31289e59b3b9144
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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