HCID 67350060, compound → HCID 67348734, compound

HRID 1676354Notes

Reaction equation

HRID 1676354 reaction equation
[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

Participants

5

Reactant 1

HCID 67350060HCID 67350060, compound

Product 1

HCID 67348734HCID 67348734, compoundYield 12.1%

Reagents, catalysts & solvents 3

HCID 165397Cupric acetate monohydrateCatalystHCID 12416832Manganese triacetate dihydrateCatalystHCID 176Acetic AcidSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-4b1f6b9350544b578b4b14b063c3b45b
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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