Chloroform → 3-Methyl-2-[4-((((3,5-dimethylphenyl)amino)carbonyl)methyl)phenoxy]butanoic acid

HRID 363234

Reaktionsgleichung

Reaktionsgleichung von HRID 363234
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:19])[CH2:11][C:12]2[CH:17]=[CH:16][C:15](O)=[CH:14][CH:13]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[OH-:20].[Na+].[CH:22](=[O:26])[CH:23]([CH3:25])[CH3:24].C(Cl)(Cl)Cl.C1[CH2:35][O:34]CC1>>[CH3:24][CH:23]([CH3:25])[CH:22]([O:26][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:10]([NH:9][C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=2)=[O:19])=[CH:13][CH:14]=1)[C:35]([OH:34])=[O:20]

Komponenten

6

Edukt 5

HCID 6212ChloroformHCID 6561IsobutyraldehydeHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 2763537N-(3,5-dimethylphenyl)-2-(4-hydroxyphenyl)acetamide

Produkt 1

HCID 154285553-Methyl-2-[4-((((3,5-dimethylphenyl)amino)carbonyl)methyl)phenoxy]butanoic acidAusbeute 23,5 %

Versuchsvorschrift

N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide (3.06 gms, 12 mmol) in THF is treated with 2.4 gms (60 mmol) of NaOH at -20° C. 5.45 ml (60 mmol) of isobutyraldehyde and 4.8 ml (60 mmol) of CHCl3 is added dropwise simultaneously at -20° C. and stirring continued overnight at room temperature. THF is removed under vacuum and the residue is dissolved in water, followed by acidification with 35% HCl. The precipitated solid is extracted into ether and treated with 6% NaHCO3 solution. The aqueous layer on acidification yields the product 3-methyl-2-[4-((((3,5-dimethylphenyl)amino)carbonyl)methyl) phenoxy] butanoic acid (C21H25NO4) (yield 1 gm, 23.5%) mp (uncorrected) 96°-100° C.

Aufarbeitung

  1. customTHF is removed under vacuum
  2. dissolutionthe residue is dissolved in water
  3. extractionThe precipitated solid is extracted into ether
  4. additiontreated with 6% NaHCO3 solution

Quellen und Nachweise

ORD-Eintrag
ord-86dd724a146a4c1993de97c70e3afe81
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872282

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