Cesium carbonate → HCID 57635040, compound

HRID 2111260Notes

Reaction equation

HRID 2111260 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11](=[O:16])[CH:12]([CH3:15])[CH2:13][NH2:14])[CH3:9].I[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.[Cu]I>[CH2:8]([O:10][C:11](=[O:16])[CH:12]([CH3:15])[CH2:13][NH:14][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:9]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 145742L-ProlineHCID 85718096HCID 85718096, compound

Product 1

HCID 57635040HCID 57635040, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4.904 g (0.020 mole) of (rac)-3-amino-2-methyl-propanoic acid ethyl ester trifluoroacetate in 30 mL of dimethylsulfoxide was added 4.08 g (0.020 mole) of iodobenzene, 0.46 g (0.004 mole) of L-proline, 0.38 g (0.002 mole) of copper (I) iodide and 19.57 g (0.060 mole) of cesium carbonate. Argon was bubbled through the solution for 15 minutes. The mixture was then heated at 80 degrees for 16 hours. After cooling, the mixture was partitioned between ethyl acetate (2×300 mL) and water (3×300 mL). The organic layers were washed with 300 mL of brine, combined, dried over anhydrous magnesium sulfate, filtered, and concentrated. Purification of the residue by silica gel chromatography, eluting with dichloromethane-hexanes (80:20) and then dichloromethane gave 1.70 g of (rac)-2-methyl-3-phenylamino-propionic acid ethyl ester as colorless oil that darkened on standing.

Workup

  1. customArgon was bubbled through the solution for 15 minutes
  2. temperatureThe mixture was then heated at 80 degrees for 16 hours
  3. temperatureAfter cooling
  4. customthe mixture was partitioned between ethyl acetate (2×300 mL) and water (3×300 mL)
  5. washThe organic layers were washed with 300 mL of brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the residue by silica gel chromatography
  10. washeluting with dichloromethane-hexanes (80:20)

Sources & evidence

ORD record
ord-43cc477dc5804c289b755e8d6d066320
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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