Dicyclohexylcarbodiimide → HCID 54100298, compound

HRID 1741925Notes

Reaction equation

HRID 1741925 reaction equation
[CH3:1][CH:2]([CH2:6][C:7]([F:10])([F:9])[F:8])[C:3](O)=[O:4].[C:11]1([C@@H:17]([NH2:19])[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C1C=CN=CC=1)C>[F:8][C:7]([F:10])([F:9])[CH2:6][CH:2]([CH3:1])[C:3]([NH:19][C@H:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:18])=[O:4]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 758181-Phenethylamine, (-)-HCID 27755364,4,4-Trifluoro-2-methylbutanoic acid

Product 1

HCID 54100298HCID 54100298, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2-methyl-4,4,4-trifluorobutanoic acid (10.0 g, 0.064 mole) in dichloromethane (150 mL) was treated with 4-(N,N-dimethylamino)-pyridine (7.8 g, 0.064 mole), and the mixture was stirred for 15 min. A solution containing (S)-1-phenylethylamine (7.8 g, 0.064 mole) in dichloromethane (50 mL) was added, the mixture was stirred for a further 15 min, and then a solution of dicyclohexylcarbodiimide (15.9 g, 0.077 mole) in dichloromethane (100 mL) was added. Stirring was continued for 15 hours, then the precipitated dicyclohexylurea was removed by filtration, and the filtrate was concentrated to an oil under reduced pressure. The oil was partitioned between 2N hydrochloric acid (100 mL) and ether (100 mL), and the two phase mixture was filtered to remove a further quantity of dicyclohexylurea. The layers were separated; and the ether fraction was washed with 2N hydrochloric acid (100 mL), 2N aqueous sodium hydroxide solution (100 mL) and saturated brine (100 mL); dried (MgSO4); and evaporated to an oil, which solidified on standing. The solid, which comprised a mixture of the two diastereomeric butyramides was used directly in the next step.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for a further 15 min
  3. stirringStirring
  4. waitwas continued for 15 hours
  5. customthe precipitated dicyclohexylurea was removed by filtration
  6. concentrationthe filtrate was concentrated to an oil under reduced pressure
  7. customThe oil was partitioned between 2N hydrochloric acid (100 mL) and ether (100 mL)
  8. filtrationthe two phase mixture was filtered
  9. customto remove a further quantity of dicyclohexylurea
  10. customThe layers were separated
  11. washand the ether fraction was washed with 2N hydrochloric acid (100 mL), 2N aqueous sodium hydroxide solution (100 mL) and saturated brine (100 mL)
  12. dry with materialdried (MgSO4)
  13. customand evaporated to an oil, which
  14. additiona mixture of the two diastereomeric butyramides

Sources & evidence

ORD record
ord-5deb61659e384f72a55387bde1050230
Source dataset
uspto-grants-1994_08
Patent number
US05334765

Reaction notes

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