Water → HCID 22327457, compound

HRID 495511Notes

Reaction equation

HRID 495511 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([NH:12][C:13]([CH3:21])([CH:18]([CH3:20])[CH3:19])[C:14]([O:16]C)=O)=[O:11].C[C:23]([O-:26])(C)C.[K+].O>C1(C)C=CC=CC=1.O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:26][CH3:23])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14](=[O:16])[C:13]([CH:18]([CH3:20])[CH3:19])([CH3:21])[NH:12][C:10]1=[O:11]

Participants

6

Reactant 3

HCID 962WaterHCID 22327456HCID 22327456, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22327457HCID 22327457, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

71.4 g (0.226 mol) of methyl N-(2-chloro-4-fluorophenylacetyl)-2-amino-2,3-dimethyl-butyrate, dissolved in 450 ml of absolute toluene, are added dropwise to a suspension of 56 g (0.498 mol) of potassium tert-butylate in 150 ml of absolute tetrahydrofuran at the boil, and stirring is continued for 90 minutes at reflux temperature. After the reaction mixture has cooled to room temperature, 700 ml of water are added, the organic phase is separated off and washed again using 340 ml of water. The combined aqueous phases are acidified at 15-20° C. using approximately 80 ml of concentrated hydrochloric acid, and the product is filtered off with suction. After drying, 57.1 g (85% of theory) of 3-(2-chloro-4-methoxyphenyl)-5-isopropyl-5-methyl-pyrrolidine-2,4-dione of m.p. 130-140° C. are obtained.

Workup

  1. temperatureat reflux temperature
  2. customthe organic phase is separated off
  3. washwashed again
  4. customare acidified at 15-20° C.
  5. filtrationthe product is filtered off with suction
  6. customAfter drying

Sources & evidence

ORD record
ord-8afb55da245e4743b7abc981ba8fe99c
Source dataset
uspto-grants-2005_09
Patent number
US06939888B2

Reaction notes

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