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

HRID 270056

Reaktionsgleichung

Reaktionsgleichung von HRID 270056
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([OH:12])[CH:3]=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>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([O:12][CH2:16][C@@H:14]2[CH2:15][O:13]2)[CH:3]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 177738N-(4-fluoro-2-hydroxyphenyl)acetamide

Produkt 1

HCID 20806548N-{4-Fluoro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamideAusbeute 59,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of N-(4-fluoro-2-hydroxyphenyl)acetamide (1.69 g, 10.0 mmol), (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (2.59 g, 10.0 mmol) and Cs2CO3 (4.87 g, 15.0 mmol) in DMF (15 mL) was stirred at room temperature for 2 h. The reaction mixture was partitioned between ethylacetate and H2O. The organic layer was dried over Na2SO4 filtered and concentrated. The residue was purified by silica gel flash chromatography to give the subtitled compound (1.35 g).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethylacetate and H2O
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c2a74e928c0541fabba85367338fbe14
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449475B2

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