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Pyridine → Methyl 2-(2,2-dimethylpropionylamino)-6-trifluoromethanesulfonyloxybenzoate

HRID 715973
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 715973
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][C:17]([CH3:33])([CH3:32])[C:18]([NH:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27](O)[C:22]=1[C:23]([O:25][CH3:26])=[O:24])=[O:19].N1C=CC=CC=1>C(Cl)Cl>[CH3:16][C:17]([CH3:33])([CH3:32])[C:18]([NH:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[C:22]=1[C:23]([O:25][CH3:26])=[O:24])=[O:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 66686167Methyl 2-hydroxy-6-pivalamidobenzoate2×

Produkt 1

HCID 86712118Methyl 2-(2,2-dimethylpropionylamino)-6-trifluoromethanesulfonyloxybenzoateAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Versuchsvorschrift

Trifluoromethanesulphonic anhydride (6.2 g) was added dropwise to an ice cooled, stirred solution of methyl 2-(2,2-dimethylpropionylamino)-6-hydroxybenzoate (Intermediate 40, 5.02 g) and pyridine (3.16 g) in DCM (70 mL) and the mixture was stirred for 1 hour. The resulting solution was washed with 2M hydrochloric acid, filtered through a phase separator and the filtrate was evaporated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-15% to give methyl 2-(2,2-dimethylpropionylamino)-6-trifluoromethanesulfonyloxybenzoate (7.09 g) as a colourless oil.

Aufarbeitung

  1. temperaturecooled
  2. washThe resulting solution was washed with 2M hydrochloric acid
  3. filtrationfiltered through a phase separator
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-15%

Quellen und Nachweise

ORD-Eintrag
ord-e5201b504afe46f58a8815cd0c816205
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09187494B2

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