Pivaloyl chloride → (2S-trans)-N-[(3,4-methylenedioxy)phenyl]-3-butyloxiranecarboxamide

HRID 2053472Notes

Reaction equation

HRID 2053472 reaction equation
[CH2:1]([C@H:5]1[O:7][C@@H:6]1[C:8]([OH:10])=O)[CH2:2][CH2:3][CH3:4].CCCCC(F)(F)C(O)CC[C@@H]1[C@@H](CCCCCCC(O)=O)C(=O)C[C@H]1O.C1CCC(NC2CCCCC2)CC1.C(Cl)(=O)C(C)(C)C.[CH2:58]1[O:67][C:66]2[CH:65]=[CH:64][C:62]([NH2:63])=[CH:61][C:60]=2[O:59]1>O1CCCC1>[CH2:58]1[O:67][C:66]2[CH:65]=[CH:64][C:62]([NH:63][C:8]([C@@H:6]3[C@@H:5]([CH2:1][CH2:2][CH2:3][CH3:4])[O:7]3)=[O:10])=[CH:61][C:60]=2[O:59]1

Participants

6

Reactant 4

HCID 62493Pivaloyl chlorideHCID 843101,3-Benzodioxol-5-amineHCID 10678368(2S-trans)-3-butyl-oxirane carboxylic acidHCID 7174909515-Hydroxy Lubiprostone Dicyclohexylammonium Salt

Product 1

HCID 86618963(2S-trans)-N-[(3,4-methylenedioxy)phenyl]-3-butyloxiranecarboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Under ice-cooling, to 10 ml of an anhydrous tetrahydrofuran solution containing 299 mg (1.84 mmol) of (2S-trans)-3-butyl-oxiranecarboxylic 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 insoluble material in the reaction mixture was filtred off, the filtrate was added to 10 ml of an anhydrous tetrahydrofuran solution containing 252 mg (1.84 mmol) of 3,4-methylenedioxyaniline under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. Under reduced pressure, the reaction mixture was concentrated, 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 484 mg (Yield: 100%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-06d00c9b4f05481e873c6af57b8b33d8
Source dataset
uspto-grants-2008_02
Patent number
US07326799B2

Reaction notes

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