Isobutyl iodide → 3-methyl-4-[2-[N-isobutyl-N-(5-methyl-2-furylsulfonyl)amino]-4,5-dimethylphenoxymethyl]benzoic Acid Methyl Ester

HRID 1866203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1866203
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([CH3:19])=[CH:14][C:13]=2[NH:20][S:21]([C:24]2[O:25][C:26]([CH3:29])=[CH:27][CH:28]=2)(=[O:23])=[O:22])=[C:6]([CH3:30])[CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:38](I)[CH:39]([CH3:41])[CH3:40].C(OCC)(=O)C.O>CN(C)C(=O)C>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([CH3:19])=[CH:14][C:13]=2[N:20]([CH2:38][CH:39]([CH3:41])[CH3:40])[S:21]([C:24]2[O:25][C:26]([CH3:29])=[CH:27][CH:28]=2)(=[O:23])=[O:22])=[C:6]([CH3:30])[CH:5]=1

Komponenten

6

Edukt 4

HCID 10556Isobutyl iodideHCID 10796Cesium carbonateHCID 22728543Water ethylacetateHCID 588919093-methyl-4-[2-[N-(5-methyl-2-furylsulfonyl)amino]4,5-dimethylphenoxymethyl]benzoic acid methyl ester

Produkt 1

HCID 588918933-methyl-4-[2-[N-isobutyl-N-(5-methyl-2-furylsulfonyl)amino]-4,5-dimethylphenoxymethyl]benzoic Acid Methyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 3-methyl-4-[2-[N-(5-methyl-2-furylsulfonyl)amino]4,5-dimethylphenoxymethyl]benzoic acid methyl ester prepared in Reference Example 3 (870 mg) in N,N-dimethylacetamide (2 ml), cesium carbonate (1.37 g) and isobutyl iodide (0.36 ml) were added and the mixture was stirred for 1 hour at 100° C. The reaction mixture was allowed to cool and poured into ethyl acetate-water (40 ml-40 ml). The organic layer was washed, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (toluene-ethyl acetate) to give the title compound (855 mg) having the following physical data.

Aufarbeitung

  1. additionwere added
  2. temperatureto cool
  3. washThe organic layer was washed
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (toluene-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-cb26ba6a38da4379a976e1ea6f8e80e3
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629369B2

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