Triethylamine → HCID 20741434, compound

HRID 348394Notes

Reaction equation

HRID 348394 reaction equation
[C:1]1([C@H:7]([N:9]2[C:13](=[O:14])[CH2:12][C@@H:11]([C:15]([OH:17])=O)[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](Cl)(=[O:22])C(Cl)=O.[CH2:24]([N:26](CC)CC)C>CN(C)C=O.ClCCl>[CH3:24][N:26]([O:22][CH3:18])[C:15]([C@@H:11]1[CH2:12][C:13](=[O:14])[N:9]([C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH3:8])[CH2:10]1)=[O:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 72363499735-43-0

Product 1

HCID 20741434HCID 20741434, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a dichloromethane solution (200 ml) of 1-[1-(R)-phenylethyl]-5-oxopyrrolidine-3-(R)-carboxylic acid (11.66 g, 0.05 mol) were added oxalyl chloride (6.54 ml, 0.075 mol) and dimethylformamide (3 drops) under ice cooling, followed by stirring at room temperature overnight. After removal of the solvent under reduced pressure, toluene (100 ml) was added thereto and the solvent was again removed under reduced pressure. To the residue were added dichloromethane (200 ml) and N,O-methylhydroxylamine hydrochloride (5.47 g, 0.055 mol), and then a dichloromethane solution (50 ml) of triethylamine (17.4 ml, 0.125 mol) was added thereto under ice cooling and stirring over a period of 15 minutes. After stirring under ice cooling for 30 minutes, the mixture was stirred at room temperature for 3 hours. The reaction solution was washed with 10% citric acid aqueous solution (100 ml), water (100 ml) and saturated sodium hydrogen carbonate aqueous solution (100 ml), successively, and then dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was subjected to silica gel column chromatography. Elution with chloroform/methanol of 50/1 to 20/1 afforded the title compound (11.32 g, 82%) as a brown oil.

Workup

  1. customAfter removal of the solvent under reduced pressure, toluene (100 ml)
  2. additionwas added
  3. customthe solvent was again removed under reduced pressure
  4. stirringunder ice cooling and stirring over a period of 15 minutes
  5. stirringAfter stirring under ice cooling for 30 minutes
  6. stirringthe mixture was stirred at room temperature for 3 hours
  7. washThe reaction solution was washed with 10% citric acid aqueous solution (100 ml), water (100 ml) and saturated sodium hydrogen carbonate aqueous solution (100 ml)
  8. dry with materialsuccessively, and then dried over anhydrous sodium sulfate
  9. customAfter removal of the solvent under reduced pressure
  10. washElution with chloroform/methanol of 50/1 to 20/1

Sources & evidence

ORD record
ord-5823d55b8c8a445a987a39350cea9203
Source dataset
uspto-grants-2007_02
Patent number
US07176313B2

Reaction notes

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