Acetic Acid → Isopropyl 3-{[3-(trifluoromethyl)phenyl]amino}-2-butenoate

HRID 639155

Reaktionsgleichung

Reaktionsgleichung von HRID 639155
O=[C:2]([CH3:10])[CH2:3][C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].[F:11][C:12]([F:21])([F:20])[C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].C(O)(=O)C>C1C=CC=CC=1>[F:11][C:12]([F:20])([F:21])[C:13]1[CH:14]=[C:15]([NH:16][C:2]([CH3:10])=[CH:3][C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5])[CH:17]=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 73753-(Trifluoromethyl)anilineHCID 68329Isopropyl acetoacetate

Produkt 1

HCID 68427757Isopropyl 3-{[3-(trifluoromethyl)phenyl]amino}-2-butenoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of 4.33 g (30 mmol) isopropyl 3-oxobutanoate in 90 ml benzene are added 4.83 g (30 mmol) 3-(trifluoromethyl)aniline and 1.80 g (30 mmol) acetic acid. The mixture is stirred under reflux for four hours using a Dean-Stark trap to remove water. After removal of the solvent in vacuo, the residue is purified by preparative HPLC (column: YMC C18 ODS-AQ 250 mm×30 mm, 11 μm; solvent A: acetonitrile, solvent B: water; gradient: 0 min 10% A, 3 min 10% A, 11 min 90% A, 13 min 90% A, 13.2 min 10% A, 15 min 10% A; wavelength: 220 nm; injection volume: ca. 900 μl ethanol solution; number of injections: 8). The product containing fractions are combined and concentrated in vacuo.

Aufarbeitung

  1. temperatureunder reflux for four hours
  2. customto remove water
  3. customAfter removal of the solvent in vacuo
  4. customthe residue is purified by preparative HPLC (column: YMC C18 ODS-AQ 250 mm×30 mm, 11 μm; solvent A: acetonitrile, solvent B: water; gradient: 0 min 10% A, 3 min 10% A, 11 min 90% A, 13 min 90% A, 13.2 min 10% A, 15 min 10% A; wavelength: 220 nm; injection volume: ca. 900 μl ethanol solution; number of injections: 8)
  5. additionThe product containing fractions
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ae36b9a8d359456384167377ce0e393f
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691854B2

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