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Water → 4-{2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-3-methyl-phenoxy}-butyric acid tert-butyl ester

HRID 448864
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 448864
[C:1]([O:5][C:6](=[O:29])[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[NH:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Br:27])[CH:21]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:33].O>CN(C=O)C>[C:1]([O:5][C:6](=[O:29])[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[N:18]([C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Br:27])[CH:21]=1)[CH3:33])([CH3:4])([CH3:2])[CH3:3]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 686025154-[2-(3-Bromo-4-chloro-benzoylamino)-3-methyl-phenoxy]-butyric acid tert-butyl ester

Produkt 1

HCID 686028104-{2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-3-methyl-phenoxy}-butyric acid tert-butyl esterAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-[2-(3-bromo-4-chloro-benzoylamino)-3-methyl-phenoxy]-butyric acid tert-butyl ester (10.2 g, 21.3 mmol) in dry DMF (100 mL) at 0° C. under N2, NaH (60% in mineral oil, 1.7 g, 42.6 mmol) was added in several portions with stirring. 10 minutes later, iodomethane (2.0 mL, 32.1 mmol) was added. The mixture was warmed to room temperature by removal of ice bath and stirring was continued for 1 hr. Water (10 mL) was then added and organics were extracted by ethyl acetate, which was then washed by water and brine, and was dried over MgSO4. After concentration, the crude product was purified by silica gel chromatography eluting with ethyl acetate/hexane (1/4) to yield 4-{2-[(3-bromo-4-chloro-benzoyl)-methyl-amino]-3-methyl-phenoxy}-butyric acid tert-butyl ester (9.5 g).

Aufarbeitung

  1. stirringstirring
  2. extractionorganics were extracted by ethyl acetate, which
  3. washwas then washed by water and brine
  4. dry with materialwas dried over MgSO4
  5. concentrationAfter concentration
  6. customthe crude product was purified by silica gel chromatography
  7. washeluting with ethyl acetate/hexane (1/4)

Quellen und Nachweise

ORD-Eintrag
ord-162701bf957f48809664ee344ec9d1c2
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08481738B2

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