Potassium Carbonate → HCID 57889791, compound

HRID 1820265Notes

Reaction equation

HRID 1820265 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:13][C@@H:14]([C:18]([OH:20])=[O:19])[CH:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>[Cu]I.CN(C=O)C>[CH2:8]([O:7][C:5]([C:4]1[CH:3]=[C:2]([NH:13][C@H:14]([CH:15]([CH3:17])[CH3:16])[C:18]([OH:20])=[O:19])[CH:12]=[CH:11][CH:10]=1)=[O:6])[CH3:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 71563D-ValineHCID 143542Ethyl 3-iodobenzoate

Product 1

HCID 57889791HCID 57889791, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Ethyl 3-iodobenzoate (857 mg, 3.10 mmol), DMF (5 mL), copper(I) iodide (65 mg, 0.34 mmol), N1,N2-dimethylaminoethylene (62.9 mg, 0.714 mmol), D-valine (400 mg, 3.41 mmol) and potassium carbonate (429 mg, 3.10 mmol) were charged into a flask. The flask was evacuated, then filled with nitrogen over several cycles to remove oxygen, then the reaction was heated to 140° C. under nitrogen for 4 hrs. The reaction was cooled, the DMF removed by evaporation, and 1 N HCl added. The reaction mixture was partitioned between EtOAc and water, and the organic layer was dried over sodium sulfate, filtered, and concentrated to yield a brown oil. This was used in next step without further purification.

Workup

  1. customThe flask was evacuated
  2. additionfilled with nitrogen over several cycles
  3. customto remove oxygen
  4. temperatureThe reaction was cooled
  5. customthe DMF removed by evaporation, and 1 N HCl
  6. additionadded
  7. customThe reaction mixture was partitioned between EtOAc and water
  8. dry with materialthe organic layer was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto yield a brown oil
  12. customThis was used in next step without further purification

Sources & evidence

ORD record
ord-8f4157a542d84288929582eddb9116c0
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

Loading…