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Sodium Chloride → 5-(2,6-Dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione

HRID 594397
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HRID 594397 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[CH:15](C(OCC)=O)[C:14](=[O:21])[C:13](=[O:22])[N:12]1[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1.[Na+].[Cl-]>CS(C)=O.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:12]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]([F:32])([F:33])[F:34])=[CH:26][CH:25]=2)[C:13](=[O:22])[C:14](=[O:21])[CH2:15]1
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참가 물질

5

반응물 2

HCID 5234Sodium ChlorideHCID 69082391Ethyl 2-(2,6-dimethoxyphenyl)-4,5-dioxo-1-(4-(trifluoromethoxy)-benzyl)pyrrolidine-3-carboxylate

생성물 1

HCID 690846265-(2,6-Dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매2회

실험 절차

A mixture of ethyl 2-(2,6-dimethoxyphenyl)-4,5-dioxo-1-(4-(trifluoromethoxy)-benzyl)pyrrolidine-3-carboxylate (11.400 g; 23.68 mmol) and NaCl (2.767 g; 47.36 mmol) in DMSO (111 ml) and water (37 ml) was refluxed, under nitrogen, for 3 h. After cooling to rt, water (150 ml) was added, and the mixture was extracted with AcOEt (3×150 ml). The mixed organic layers were washed with brine (50 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Addition of Et2O and trituration allowed the precipitation of the product. Subsequent filtration, and drying of the obtained solid under HV afforded 5-(2,6-dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione as a pink solid. LC-MS (conditions A): tR=0.85 min.; [M+H]+: 410.15 g/mol.

후처리

  1. temperaturewas refluxed, under nitrogen, for 3 h
  2. extractionthe mixture was extracted with AcOEt (3×150 ml)
  3. washThe mixed organic layers were washed with brine (50 ml)
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. additionAddition of Et2O and trituration
  8. customthe precipitation of the product
  9. filtrationSubsequent filtration
  10. customdrying of the obtained solid under HV

출처 및 근거

ORD 기록
ord-8e1d897773b54a5eb88f0126f915acbc
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242970B2

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