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

HRID 2053467
Notes
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Reaction equation

HRID 2053467 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.[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fb5bda76079041c4a5de58430c344839
Source dataset
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07326799B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes