Cesium carbonate → 4-{[(1-tert-Butoxycarbonyl-2-methyl-propyl)-(4-methoxy-benzenesulfonyl)-amino]-methyl}benzoic acid methyl ester

HRID 1517167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517167
[C:1]([O:5][C:6](=[O:23])[CH:7]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:31][C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=1.CCOC(C)=O.CCCCCC>C(#N)C>[CH3:39][O:38][C:36](=[O:37])[C:35]1[CH:40]=[CH:41][C:32]([CH2:31][N:11]([CH:7]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:23])[CH:8]([CH3:10])[CH3:9])[S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:33][CH:34]=1

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 10783604Tert-butyl 2-{[(4-methoxyphenyl)sulfonyl]amino}-3-methylbutanoateHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 694513514-{[(1-tert-Butoxycarbonyl-2-methyl-propyl)-(4-methoxy-benzenesulfonyl)-amino]-methyl}benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirring solution of 2-(4-Methoxy-benzenesulfonylamino)-3-methyl-butyric acid tert-butyl ester (140 mg, 0.41 mmol) in acetonitrile (5 ml) at ambient temperature was added cesium carbonate (1.33 g, 4.10 mmol). Then methyl 4-(bromomethyl)benzoate (115 mg, 0.60 mmol) was added to the suspension and the reaction mixture was stirred at 70° C. for 1 hour by which time TLC (EtOAc/Hexane 1:1) monitoring showed the reaction to be completed. After cooling to ambient temperature, the mixture was filtered to remove excess cesium carbonate and evaporated to dryness. The residue was purified by flash chromatography (EtOAc/Hexane 1:1) to furnish the pure product as slightly yellow oil. Yield 153 mg (76%).

Aufarbeitung

  1. customthe reaction
  2. filtrationthe mixture was filtered
  3. customto remove excess cesium carbonate
  4. customevaporated to dryness
  5. customThe residue was purified by flash chromatography (EtOAc/Hexane 1:1)
  6. customto furnish the pure product as slightly yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-d1c7cde57d4f4aa6b90c33b9b31956b2
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08231858B2

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