HCID 67350060, Verbindung → HCID 67348734, Verbindung

HRID 1676354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676354
[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 allowed to stir for 3 days at room temperature. The reaction was 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 power. LRMS (APCI pos) m/e 250.1 (M+1). 1H NMR: (CDCl3, 400 MHz) δ 7.49-7.54 (m, 2H), 7.02-7.07 (m, 2H), 4.02-4.07 (m, 1H), 3.83 (s, 3H), 3.70 (d, 1H), 2.45-2.53 (m, 1H), 2.02-2.09 (m, 1H), 1.29-1.33 (m, 1H).

Aufarbeitung

  1. customThe reaction was quenched 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-4b1f6b9350544b578b4b14b063c3b45b
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003662B2

Notizen zur Reaktion

Wird geladen…