Tetronic acid → HCID 57908390, compound

HRID 425740Notes

Reaction equation

HRID 425740 reaction equation
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=O.[Cl:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][NH:16][CH2:17][CH2:18][CH2:19][F:20])=[CH:11][CH:10]=1>C(O)(=O)C>[Cl:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][N:16]([CH2:17][CH2:18][CH2:19][F:20])[C:2]2[CH2:4][O:5][C:6](=[O:7])[CH:1]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 521261Tetronic acidHCID 87118536HCID 87118536, compound

Product 1

HCID 57908390HCID 57908390, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.52 g (5.18 mmol) of tetronic acid is initially charged in 1.13 ml of acetic acid, and 1.00 g (4.93 mmol) of N-[(6-chloropyridin-3-yl)methyl]-3-fluoropropane-1-amine (III-2) is added slowly at room temperature. The entire reaction mixture is then stirred at room temperature for approximately a further 18 hours. The reaction mixture is concentrated under reduced pressure, the residue is then taken up in dichloromethane and the mixture is washed with water. After phase separation, the aqueous phase is extracted twice with dichloromethane. The combined organic phases are then made alkaline (pH>9) with 1 N sodium hydroxide solution and the phases are separated. The aqueous phase is extracted twice with dichloromethane, and, after phase separation, the combined organic phases are dried over sodium sulphate. Concentration of the organic phase under reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60—Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (9:1) gives 191 mg (14% of theory) of 4-[[(6-chloropyridin-3-yl)methyl](3-fluoro-n-propyl)amino]furan-2(5H)-one.

Workup

  1. customThe entire reaction mixture
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. washthe mixture is washed with water
  4. customAfter phase separation
  5. extractionthe aqueous phase is extracted twice with dichloromethane
  6. customthe phases are separated
  7. extractionThe aqueous phase is extracted twice with dichloromethane
  8. customafter phase separation
  9. dry with materialthe combined organic phases are dried over sodium sulphate
  10. customConcentration of the organic phase under reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60—Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-1205ae36f60d47c5a9c294d2340d919d
Source dataset
uspto-grants-2012_01
Patent number
US08106211B2

Reaction notes

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