Triethylamine → HCID 42604211, compound

HRID 2093013Notes

Reaction equation

HRID 2093013 reaction equation
[K+].[CH2:2]([C@@H:5]1[O:7][C@H:6]1[C:8]([O-:10])=O)[CH2:3][CH3:4].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[CH:25]1([NH2:28])[CH2:27][CH2:26]1>CC(C)=O.C1(C)C=CC=CC=1.O>[CH:25]1([NH:28][C:8]([C@H:6]2[C@H:5]([CH2:2][CH2:3][CH3:4])[O:7]2)=[O:10])[CH2:27][CH2:26]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 69828CyclopropylamineHCID 23679017HCID 23679017, compound

Product 1

HCID 42604211HCID 42604211, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
3 °C

Procedure

200 g of trans-3-n-propyloxiranecarboxylic acid potassium salt are suspended in 2 l of acetone, admixed with 120 g of triethylamine and cooled to 3° C. 146 g of pivaloyl chloride are then added, and the mixture is stirred at 20° C. for 20 minutes and then cooled to 3° C. To this are added 82 g of cyclopropylamine in 175 ml of acetone. After stirring for 20 min, the solution is drawn off in vacuo, and the residue is dissolved in 2 l of toluene and 400 ml of water, and the pH is adjusted to 10. The aqueous phase is removed and the organic phase is admixed with 300 ml of water and the pH is adjusted to 2 with hydrochloric acid. The organic phase is removed and concentrated in vacuo. 175 g of N-cyclopropyl-trans-3-n-propyloxiranecarboxamide are obtained as a light brown oil.

Workup

  1. temperaturecooled to 3° C
  2. stirringAfter stirring for 20 min
  3. customThe aqueous phase is removed
  4. customThe organic phase is removed
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb6e7796c9c74a08a49adce31c1d6f3c
Source dataset
uspto-grants-2013_05
Patent number
US08440862B2

Reaction notes

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