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Pivaloyl chloride → (2S)-trans-N-[(1S,2S)-2-hydroxycyclohexane-1-yl]-3-butyloxiranecarboxamide

HRID 1698427
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1698427
[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.[NH2:58][C@H:59]1[CH2:64][CH2:63][CH2:62][CH2:61][C@@H:60]1[OH:65]>O1CCCC1>[OH:65][C@H:60]1[CH2:61][CH2:62][CH2:63][CH2:64][C@@H:59]1[NH:58][C:8]([C@@H:6]1[C@@H:5]([CH2:1][CH2:2][CH2:3][CH3:4])[O:7]1)=[O:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 62493Pivaloyl chlorideHCID 7057408(1S,2S)-2-aminocyclohexanolHCID 10678368(2S-trans)-3-butyl-oxirane carboxylic acidHCID 7174909515-Hydroxy Lubiprostone Dicyclohexylammonium Salt

Produkt 1

HCID 86618962(2S)-trans-N-[(1S,2S)-2-hydroxycyclohexane-1-yl]-3-butyloxiranecarboxamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Under ice-cooling, to 20 ml of an anhydrous tetrahydrofuran solution containing 2.3 g (7 mmol) of (2S-trans)-3-butyl-oxirane carboxylic acid.dicyclohexylammonium salt was added 2 ml of an anhydrous tetrahydrofuran solution containing 844 mg (7 mmol) of pivaloyl chloride, and the 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 further stirred for 2 hours. After removing insoluble material in the reaction mixture by filtration, the filtrate was added to 20 ml of an anhydrous tetrahydrofuran solution containing 806 mg (7 mmol) of (1S,2S)-2-aminocyclohexanol under ice-cooling, 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 1.69 g (Yield: 100%) of the title compound.

Aufarbeitung

  1. customwas returned to room temperature
  2. stirringthe mixture was further stirred for 2 hours
  3. customAfter removing insoluble material in the reaction mixture
  4. filtrationby filtration
  5. additionthe filtrate was added to 20 ml of an anhydrous tetrahydrofuran solution
  6. temperaturecooling
  7. stirringthe resulting mixture was stirred at room temperature for 2 hours
  8. concentrationUnder reduced pressure, the reaction mixture was concentrated
  9. additionethyl acetate was added to the concentrate
  10. washthe resulting mixture was washed successively with a 10% aqueous potassium hydrogen sulfate solution
  11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  12. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ca9dda6e15a0485e92bd891aa9e3d56f
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163943B2

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