Hydrochloric Acid → 5-(2,2-Difluorovinyl)-N-methyl-N-propyl-isophthalamic acid

HRID 1436642

Reaktionsgleichung

Reaktionsgleichung von HRID 1436642
C([O:3][C:4](=[O:22])[C:5]1[CH:17]=[C:16]([CH:18]=[C:19]([F:21])[F:20])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)C.[OH-].[Li+].Cl>C1COCC1>[F:20][C:19]([F:21])=[CH:18][C:16]1[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=[C:5]([CH:17]=1)[C:4]([OH:22])=[O:3]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 688145195-(2,2-Difluorovinyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester

Produkt 1

HCID 688140405-(2,2-Difluorovinyl)-N-methyl-N-propyl-isophthalamic acidAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Stir a solution of 5-(2,2-difluorovinyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester (187 mg, 0.63 mmol), 1 N lithium hydroxide (2.5 mL, 2.5 mmol) and THF (2.5 mL) at room temperature overnight. Partition the reaction between ethyl acetate and water. Acidify the aqueous with 5 N HCl and extract with ethyl acetate. Dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 2:98 to 6:94 methanol:dichloromethane with 1% acetic acid) to give the title compound (78 mg, 44%).

Aufarbeitung

  1. customPartition
  2. customthe reaction between ethyl acetate and water
  3. extractionextract with ethyl acetate
  4. dry with materialDry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 2:98 to 6:94 methanol:dichloromethane with 1% acetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-f52d462cb0b645ce8f9d4ddf6f3121f0
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618978B2

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