HCID 67350060, compound → HCID 67348734, compound

HRID 2241327Notes

Reaction equation

HRID 2241327 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 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).

Workup

  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)

Sources & evidence

ORD record
ord-85230efec424447d9987ee31beb3bf0c
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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