Hydrochloric Acid → HCID 22618723, compound

HRID 842290Notes

Reaction equation

HRID 842290 reaction equation
[OH-].[K+].[CH2:3]([C:5]1([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:15][CH:14]=2)[CH2:9][O:8]C(=O)[NH:6]1)[CH3:4].[ClH:30]>O.CO.O1CCCC1.CCOCC>[ClH:30].[NH2:6][C:5]([CH2:3][CH3:4])([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:15][CH:14]=1)[CH2:9][OH:8]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22618862HCID 22618862, compound

Product 1

HCID 22618723HCID 22618723, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of potassium hydroxide (5.8 g) in water (20 ml) was added to a solution of 4-ethyl-4-(2-(4-(4-phenylbutyloxy)phenyl)ethyl)oxazolidin-2-one (3.0 g) in methanol (60 ml) and tetrahydrofuran (50 ml). The mixture was refluxed under heating for 18.5 hours while stirring. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure to give a pale brown, oily substance. The oily substance was subjected to silica gel column chromatography (eluent; ethyl acetate then methanol) and the solvent was distilled away to give a pale brown residue. The obtained residue was dissolved in methanol and thereto was added a 1M solution of hydrochloric acid in ether. The solution was concentrated under reduced pressure, and the obtained crude crystals were recrystallized from isopropyl ether and hexane to give the subject compound (0.63 g) as white crystals, melting at 101-103° C.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 18.5 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customto give a pale brown, oily substance
  8. distillationethyl acetate then methanol) and the solvent was distilled away
  9. customto give a pale brown residue
  10. concentrationThe solution was concentrated under reduced pressure
  11. customthe obtained crude crystals
  12. customwere recrystallized from isopropyl ether and hexane

Sources & evidence

ORD record
ord-b84afed60fdd440fb86694e9122821b2
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

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