HCID 67350060, Verbindung → HCID 67348734, Verbindung

HRID 2241327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2241327
[CH2:1]([N:4]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[C:5](=[O:11])[CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH:2]=[CH2:3]>C(O)(=O)C.O.O.C([O-])(=O)C.[Mn+3].C([O-])(=O)C.C([O-])(=O)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:18][C:15]1[CH:16]=[CH:17][C:12]([N:4]2[CH2:1][CH:2]3[C:6]([C:7]([O:9][CH3:10])=[O:8])([CH2:3]3)[C:5]2=[O:11])=[CH:13][CH:14]=1

Komponenten

5

Edukt 1

HCID 67350060HCID 67350060, Verbindung

Produkt 1

HCID 67348734HCID 67348734, VerbindungAusbeute 12,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 165397Cupric acetate monohydrateKatalysatorHCID 12416832Manganese triacetate dihydrateKatalysatorHCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

A solution of methyl 3-(allyl(4-fluorophenyl)amino)-3-oxopropanoate (10 g, 39.7 mmol) in acetic acid (50 mL) was added into a suspension of manganese(III)acetate dihydrate (21 g, 79.7 mmol) and copper (II) acetate monohydrate (7.9 g, 39.7 mmol) in acetic acid (200 mL). The reaction was stirred for 3 days, then quenched with 10% aqueous sodium bisulfite solution (100 mL). The reaction mixture was diluted with EtOAc, washed with saturated aqueous NaHCO3, brine, dried with Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (50% EtOAc in hexane) to afford the product (1.2 g, 12% yield) as a brown powder. LRMS (APCI pos) m/e 250.1 (M+1).

Aufarbeitung

  1. customquenched with 10% aqueous sodium bisulfite solution (100 mL)
  2. additionThe reaction mixture was diluted with EtOAc
  3. washwashed with saturated aqueous NaHCO3, brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (50% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-85230efec424447d9987ee31beb3bf0c
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723330B2

Notizen zur Reaktion

Wird geladen…