Water → HCID 22327527, compound

HRID 495510Notes

Reaction equation

HRID 495510 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH2:10][C:11]([NH:13][C:14]([CH3:22])([CH:19]([CH3:21])[CH3:20])[C:15]([O:17]C)=O)=[O:12].CC([O-])(C)C.[K+].O>C1(C)C=CC=CC=1.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH:10]1[C:15](=[O:17])[C:14]([CH:19]([CH3:21])[CH3:20])([CH3:22])[NH:13][C:11]1=[O:12]

Participants

6

Reactant 3

HCID 962WaterHCID 22327551HCID 22327551, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22327527HCID 22327527, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

23.8 g (0.073 mol) of methyl N-(2-chloro-6-methoxyphenylacetyl)-2-amino-2,3-dimethyl-butyrate, dissolved in 150 ml of absolute toluene, are added dropwise to a suspension of 18.06 g (0.16 mol) of potassium tert-butylate in 50 ml of absolute tetrahydrofuran at the boil, and the mixture was heated at reflux temperature for 1.5 hours. After the reaction mixture has cooled to room temperature, 230 ml of water are added, the aqueous phase is separated off, the toluene phase is reextracted using 110 ml of water, and the combined aqueous phases are acidified at 15-20° C. using approximately 25 ml of concentrated hydrochloric acid. The product is filtered off with suction and dried. 20.2 g (93% of theory) of 3-(2-chloro-6-methoxyphenyl)-5-isopropyl-5-methyl-pyrrolidine-2,4-dione of m.p. 172-174° C. are obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 1.5 hours
  3. customthe aqueous phase is separated off
  4. customare acidified at 15-20° C.
  5. filtrationThe product is filtered off with suction
  6. customdried

Sources & evidence

ORD record
ord-8a98e5c309fa453c8a6075e55dd7503c
Source dataset
uspto-grants-2005_09
Patent number
US06939888B2

Reaction notes

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