18-Crown-6 → (2-Fluoro-6-nitrophenylamino)acetic acid ethyl ester

HRID 558940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 558940
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1F.Cl.[CH2:13]([O:15][C:16](=[O:19])[CH2:17][NH2:18])[CH3:14].[F-].[K+].C1OCCOCCOCCOCCOCCOC1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:13]([O:15][C:16](=[O:19])[CH2:17][NH:18][C:3]1[C:4]([N+:8]([O-:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[CH3:14]

Komponenten

7

Edukt 5

HCID 2855718-Crown-6HCID 813351,2-Difluoro-3-nitrobenzeneHCID 81531DiisopropylethylamineHCID 522689Potassium FluorideHCID 2723640Glycine ethyl ester, hydrochloride

Produkt 1

HCID 67000141(2-Fluoro-6-nitrophenylamino)acetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 1,2-difluoro-3-nitrobenzene from Example B1 (1.9 g, 12 mmol) in acetonitrile (75 ml) were added glycine ethyl ester hydrochloride (1.7 g, 12 mmol), potassium fluoride (1.2 g, 20 mmol), 18-crown-6 (309 mg, 1.2 mmol) and diisopropylethylamine (4.6 ml, 26 mmol). The mixture was stirred at reflux for 3 h, cooled and evaporated in vacuo. The residue was partitioned between water and EtOAc. The organic layer was washed with brine, filtered and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 20:80); yield 2.1 g, 73%.

Aufarbeitung

  1. temperatureat reflux for 3 h
  2. temperaturecooled
  3. customevaporated in vacuo
  4. customThe residue was partitioned between water and EtOAc
  5. washThe organic layer was washed with brine
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 20:80)

Quellen und Nachweise

ORD-Eintrag
ord-9f4ca0a11f0c4f95b0e06008b165e582
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063038B2

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