Glycine → HCID 86691100, compound

HRID 1406307Notes

Reaction equation

HRID 1406307 reaction equation
NCC(O)=O.[NH:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:20][C:21]1[CH:22]=[CH:23][C:24](I)=[C:25]([C:27](=[O:29])[CH3:28])[CH:26]=1>[Cu]I>[C:27]([C:25]1[CH:26]=[C:21]([F:20])[CH:22]=[CH:23][C:24]=1[N:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 750GlycineHCID 120252-PyrrolidoneHCID 62657Potassium Phosphate, TribasicHCID 299348811-(5-Fluoro-2-iodophenyl)ethan-1-one

Product 1

HCID 86691100HCID 86691100, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

1,4-Dioxane (50 mL) was degassed by heating briefly to reflux and bubbling nitrogen gas through the solvent for 10 minutes, whilst it cooled to room temperature. CuI (180 mg, 5 mol %), glycine (284 mg, 20 mol %), 2-pyrrolidinone (1.73 mL, 22.73 mmol), K3PO4 (10.05 g, 47.35 mmol) and 1-(5-fluoro-2-iodo-phenyl)-ethanone (5.0 g, 18.94 mmol) were added sequentially to the solvent and the reaction mixture was heated at 100° C. under N2 for 10 hours. The reaction mixture was filtered through a celite plug, eluting with EtOAc and the filtrate was concentrated. The crude product was purified by flash chromatography (5% MeOH in DCM) to give the title compound (2.02 g, 48% yield) as a yellow oil

Workup

  1. custom1,4-Dioxane (50 mL) was degassed
  2. temperatureby heating briefly
  3. temperatureto reflux
  4. custombubbling nitrogen gas through the solvent for 10 minutes
  5. temperaturethe reaction mixture was heated at 100° C. under N2 for 10 hours
  6. filtrationThe reaction mixture was filtered through a celite plug
  7. washeluting with EtOAc
  8. concentrationthe filtrate was concentrated
  9. customThe crude product was purified by flash chromatography (5% MeOH in DCM)

Sources & evidence

ORD record
ord-e28cbea3d64c4ee099e1e20301db4815
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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