Ethyl chloroformate → 4-Fluoro-2-{2-fluoro-4-[(3-oxopiperazin-1-yl)carbonyl]phenoxy}-5-ethylphenyl ethyl carbonate

HRID 389983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389983
[CH2:1]([C:3]1[C:25]([F:26])=[CH:24][C:6]([O:7][C:8]2[CH:22]=[CH:21][C:11]([C:12]([N:14]3[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]3)=[O:13])=[CH:10][C:9]=2[F:23])=[C:5]([O:27][CH3:28])[CH:4]=1)[CH3:2].[OH-:29].[K+].[CH2:31]([O:33]C(Cl)=O)[CH3:32]>C(#N)C>[C:28](=[O:29])([O:33][CH2:31][CH3:32])[O:27][C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[C:25]([F:26])=[CH:24][C:6]=1[O:7][C:8]1[CH:22]=[CH:21][C:11]([C:12]([N:14]2[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]2)=[O:13])=[CH:10][C:9]=1[F:23]

Komponenten

5

Edukt 3

HCID 10928Ethyl chloroformateHCID 14797Potassium HydroxideHCID 671162484-[4-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoyl]piperazin-2-one

Produkt 1

HCID 513565044-Fluoro-2-{2-fluoro-4-[(3-oxopiperazin-1-yl)carbonyl]phenoxy}-5-ethylphenyl ethyl carbonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 4-[4-(4-ethyl-5-fluoro-2-hydroxyphenoxy)-3-fluorobenzoyl]piperazin-2-one (20 mg, 0.053 mmol; which may be prepared as described in D3) in acetonitrile (550 μL) was added KOH (3 mg, 0.053 mmol) followed by ethylchlorocarbonate (6 μL, 0.058 mmol). After 1 hour at room temperature, the mixture was quenched with water. The aqueous layer was extracted twice with ethyl acetate. The organic phase was dried over sodium sulphate, filtered and concentrated under vacuum. The residue was purified by preparative thin layer chromatography on silica gel, using dichloromethane/methanol (95:5) as eluent. The title product was obtained as a white solid (11 mg, 46%).

Aufarbeitung

  1. customthe mixture was quenched with water
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by preparative thin layer chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4e9787902e424e06ab405efcccdf09a7
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383621B2

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