Cesium carbonate → HCID 86601480, Verbindung

HRID 270072

Reaktionsgleichung

Reaktionsgleichung von HRID 270072
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1.[O:13]1[CH2:15][C@H:14]1[CH2:16]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:16][C@@H:14]2[CH2:15][O:13]2)=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 952582-Acetylamino-4-chlorophenolHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Produkt 1

HCID 86601480HCID 86601480, VerbindungAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of N-(5-chloro-2-hydroxyphenyl)acetamide (500 mg, 2.69 mmol), (2S)-oxiran-2-ylmethyl3-nitrobenzenesulfonate (697 mg, 2.69 mmol) and Cs2CO3 (1.04 g, 3.22 mmol) in DMF (10 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-50% ethyl acetate in petroleum ether) to give the subtitled compound (600 mg).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography (0-50% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-ba1e445f47844faaa2ea1eba40902c38
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449475B2

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