3,3,3-Trifluoropropionic acid → N-(4-chloro-3-methylisothiazol-5-yl)-2-[4-hydroxy-3-(3,3,3-trifluoropropionamido)phenyl]propionamide

HRID 48161

Reaktionsgleichung

Reaktionsgleichung von HRID 48161
[Cl:1][C:2]1[C:3]([CH3:20])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:19])[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([NH2:18])[CH:12]=1)[CH3:10].[F:21][C:22]([F:28])([F:27])[CH2:23][C:24](O)=[O:25].Cl.C(N(CC)CCCN=C=NCC)C>CN(C)C(=O)C>[Cl:1][C:2]1[C:3]([CH3:20])=[N:4][S:5][C:6]=1[NH:7][C:8](=[O:19])[CH:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([NH:18][C:24](=[O:25])[CH2:23][C:22]([F:28])([F:27])[F:21])[CH:12]=1)[CH3:10]

Komponenten

5

Edukt 3

HCID 27779723,3,3-Trifluoropropionic acidHCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochlorideHCID 22742099N-(4-chloro-3-methylisothiazol-5-yl)-2-(3-amino-4-hydroxyphenyl)propionamide

Produkt 1

HCID 22742118N-(4-chloro-3-methylisothiazol-5-yl)-2-[4-hydroxy-3-(3,3,3-trifluoropropionamido)phenyl]propionamideAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A mixture of N-(4-chloro-3-methylisothiazol-5-yl)-2-(3-amino-4-hydroxyphenyl)propionamide (0.65 g, 0.002 mol), 3,3,3-trifluoropropionic acid (0.267 g, 0.002 mol) and 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.40 g, 0.002 mol) was stirred in N,N-dimethylacetamide (8 ml) at room temperature for 7 hours and was then allowed to stand at room temperature overnight. The reaction was quenched with water and extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate:hexane 1:1, to give N-(4-chloro-3-methylisothiazol-5-yl)-2-[4-hydroxy-3-(3,3,3-trifluoropropionamido)phenyl]propionamide (0.62 g) as a white solid.

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluting with ethyl acetate:hexane 1:1

Quellen und Nachweise

ORD-Eintrag
ord-4c9a56a369914b5eb3b3ecfbd160c61f
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703347B2

Verknüpfte Notizen

Wird geladen…