Water → HCID 86705170, compound

HRID 2401267Notes

Reaction equation

HRID 2401267 reaction equation
O[CH2:2][C@@H:3]([NH:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[O:9])[CH2:4][CH2:5][CH3:6].CC(C)([O-])C.[K+].O>C1COCC1>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([N:10]2[CH2:2][C@H:3]([CH2:4][CH2:5][CH3:6])[NH:7][C:8]2=[O:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86705169HCID 86705169, compound

Product 1

HCID 86705170HCID 86705170, compoundYield 6.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-[(2S)-1-hydroxypentan-2-yl]-3-(4-methoxyphenyl)urea (550 mg) and potasium tert-butoxide (593 mg) in THF (25 mL) was cooled in ice under nitrogen atomosphere, and a solution of p-toluenesulfonylchrolide (672 mg) in THF (10 mL) was added dropwise thereto. After the mixture was stirred for 1 hr while cooling in ice, water was added thereto, and the resulting mixture was extracted with chloroform. The organic layer was separated out by phase-separation cartridge, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=88:12-0:100), and further recrystallized from chloroform/hexane. The solid was collected by filtration to afford (4S)-1-(4-methoxyphenyl)-4-propylimidazolidin-2-one (34 mg). In addition, the filtrate was concentrated under reduced pressure to afford (4S)-1-(4-methoxyphenyl)-4-propylimidazolidin-2-one (254 mg).

Workup

  1. temperaturewhile cooling in ice
  2. extractionthe resulting mixture was extracted with chloroform
  3. customThe organic layer was separated out by phase-separation cartridge
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=88:12-0:100)
  6. customfurther recrystallized from chloroform/hexane
  7. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-bb258deaf54346349929cf1f1906e6ee
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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