Sodium hydride → Methyl 2-fluoro-5-nitro-3-(2-oxo-1-pyrrolidinyl)benzoate

HRID 852582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852582
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[C:9]([F:21])=[C:10]([CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:6].[H-].[Na+]>C1COCC1.CCOC(C)=O>[F:21][C:9]1[C:8]([N:7]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])=[CH:17][C:16]([N+:18]([O-:20])=[O:19])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Komponenten

5

Edukt 2

HCID 24758Sodium hydrideHCID 69358882Methyl 3-[(4-chlorobutanoyl)amino]-2-fluoro-5-nitrobenzoate

Produkt 1

HCID 69360218Methyl 2-fluoro-5-nitro-3-(2-oxo-1-pyrrolidinyl)benzoateAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-[(4-chlorobutanoyl)amino]-2-fluoro-5-nitrobenzoate (D139) (8.5 g, 26.7 mmol, 1 equiv) in THF (100 ml) was added NaH (60% dispersion in mineral oil, 1.17 g, 29.4 mmol, 1.1 equiv) and the resulting mixture was stirred at room temperature for 1.5 h then diluted with AcOEt. The organic phase was washed with H2O, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 2/1) gave methyl 2-fluoro-5-nitro-3-(2-oxo-1-pyrrolidinyl)benzoate (D140) (3.3 g, 43%) as a yellow solid. [M+H]+=283.1, RT=2.53 min.

Aufarbeitung

  1. washThe organic phase was washed with H2O
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 2/1)

Quellen und Nachweise

ORD-Eintrag
ord-55f0fd4440af41af8f5e2815f87c9a9a
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253198B2

Notizen zur Reaktion

Wird geladen…