Tetrahydrofuran → (2S-trans)-N-[(2S)-1-methoxy-1-oxo-3-phenyl-2-propyl]-3-butyloxiranecarboxamide

HRID 2053479Notes

Reaction equation

HRID 2053479 reaction equation
[C:1](Cl)(=[O:6])[C:2](C)(C)[CH3:3].C(N([CH2:13][CH3:14])CC)C.Cl.[CH3:16][O:17][C:18](=[O:28])[C@H:19]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH2:20].[O:29]1CC[CH2:31][CH2:30]1>>[CH3:16][O:17][C:18](=[O:28])[C@@H:19]([NH:20][C:30]([C@@H:31]1[C@@H:1]([CH2:2][CH2:3][CH2:13][CH3:14])[O:6]1)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 75736Methyl L-phenylalaninate hydrochloride

Product 1

HCID 86618965(2S-trans)-N-[(2S)-1-methoxy-1-oxo-3-phenyl-2-propyl]-3-butyloxiranecarboxamideYield 100%

Procedure

Under ice-cooling, to 10 ml of an anhydrous tetrahydrofuran solution containing 299 mg (1.84 mmol) of (2S-trans)-3-butyloxirane carboxylic acid•dicyclohexylammonium salt was added 2 ml of an anhydrous tetrahydrofuran solution containing 222 mg (1.84 mmol) of pivaloyl chloride, and the resulting mixture was stirred at the same temperature for 15 minutes. Moreover, the temperature of the reaction mixture was returned to room temperature and the mixture was stirred for 2 hours. After filtering off insoluble materials in the reaction mixture, 187 mg (1.84 mmol) of triethylamine was added to the filtrate under ice-cooling, and then, 397 mg (1.84 mmol) of L-phenylalanine methyl ester hydrochloride was added to the mixture, and the resulting mixture was stirred at room temperature for 2 hours. Under reduced pressure, the reaction mixture was concentrated and ethyl acetate was added to the concentrate, and the resulting mixture was washed successively with a 10% aqueous potassium hydrogen sulfate solution, a saturated aqueous sodium hydrogen carbonate solution and then a saturated NaCl solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 558 mg (Yield: 100%) of the title compound.

Workup

  1. customwas returned to room temperature
  2. stirringthe mixture was stirred for 2 hours
  3. additionwas added to the filtrate under ice-
  4. temperaturecooling
  5. stirringthe resulting mixture was stirred at room temperature for 2 hours
  6. concentrationUnder reduced pressure, the reaction mixture was concentrated
  7. additionethyl acetate was added to the concentrate
  8. washthe resulting mixture was washed successively with a 10% aqueous potassium hydrogen sulfate solution
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5edae6422b8d462ca22b0168ce89b420
Source dataset
uspto-grants-2008_02
Patent number
US07326799B2

Reaction notes

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