Cesium carbonate → N-{4-Chloro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide

HRID 270074

Reaktionsgleichung

Reaktionsgleichung von HRID 270074
[O:1]1[CH2:3][C@H:2]1[CH2:4]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[C:21]([OH:29])[CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[C:21]([O:29][CH2:4][C@@H:2]2[CH2:3][O:1]2)[CH:20]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 177739N-(4-Chloro-2-hydroxyphenyl)acetamide

Produkt 1

HCID 86601481N-{4-Chloro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamideAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of (2S)-oxiran-2ylmethyl3-nitrobenzenesulfonate (3.37 g, 13.25 mmol), N-(4-chloro-2-hydroxyphenyl)acetamide (2.46 g, 17.23 mmol) and Cs2CO3 (6.48 g, 19.88 mmol) was added DMF (20 mL) at 0° C. and the reaction mixture was stirred at 0° C. for 3 h. 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 (hexane:ethyl acetate 3:2) to give the subtitled compound (2.36 g).

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 (hexane:ethyl acetate 3:2)

Quellen und Nachweise

ORD-Eintrag
ord-62d08c44daf2470caad11857e41ea86f
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449475B2

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