Acetone → 3-Dibenzylamino-2,6-difluoro-benzoic acid benzyl ester

HRID 38103

Reaktionsgleichung

Reaktionsgleichung von HRID 38103
[CH2:1]([N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.C([Li])CCC.Cl[C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35]>O1CCCC1.O>[CH2:37]([O:36][C:34](=[O:35])[C:11]1[C:12]([F:15])=[CH:13][CH:14]=[C:9]([N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10]=1[F:16])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 10387Benzyl chloroformateHCID 58086650Dibenzyl-(2,4-difluoro-phenyl)-amineHCID 178418339Butyllithium

Produkt 1

HCID 584771183-Dibenzylamino-2,6-difluoro-benzoic acid benzyl esterAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To dibenzyl-(2,4-difluoro-phenyl)-amine (3.097 g, 10.02 mmol) in tetrahydrofuran (45 mL), under nitrogen atmosphere, cooled at −78° C. acetone/dry in ice bath, n-butyllithium (1.6 M in hexane, 6.88 mL, 11.02 mmol) was added slowly. The reaction was stirred for 1 hour, benzyl chloroformate (1.54 mL, 11.02 mmol) was added and the reaction was allowed to warm to room temperature during 2 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 5% ethyl acetate in hexane grading to 10% acetate to provide the title compound as colourless oil (4.0 g, 90%).

Aufarbeitung

  1. customdry in ice bath
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 5% ethyl acetate in hexane grading to 10% acetate

Quellen und Nachweise

ORD-Eintrag
ord-017853bc57484144b02dcfab4738d4c4
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524707B2

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