Triethylamine → HCID 20741434, compound

HRID 2417243Notes

Reaction equation

HRID 2417243 reaction equation
[C:1](Cl)(=[O:5])C(Cl)=O.[C:7]1([C@H:13]([N:15]2[C:19](=[O:20])[CH2:18][C@@H:17]([C:21]([OH:23])=O)[CH2:16]2)[CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:24]([N:26](CC)CC)C>CN(C)C=O.ClCCl>[CH3:24][N:26]([O:5][CH3:1])[C:21]([C@@H:17]1[CH2:18][C:19](=[O:20])[N:15]([C@@H:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:14])[CH2:16]1)=[O:23]

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

Oxalyl chloride (6.54 ml, 0.075 mol) and dimethylformamide (3 drops) were added to ice-cooled dichloromethane solution (200 ml) of 1-[1-(R)-phenylethyl]-5-oxopyrrolidine-3-(R)-carboxylic acid (11.66 g, 0.05 mol), and the mixture was stirred overnight at room temperature. After evaporation of the solvent under a reduced pressure, toluene (100 ml) was added and the solvent was again evaporated under a reduced pressure. Dichloromethane (200 ml) and N,O-methylhydroxylamine hydrochloride (5.47 g, 0.055 mol) were added to the resulting residue and, while ice-cooling and stirring, dichloromethane solution (50 ml) of triethylamine (17.4 ml, 0.125 mol) was added dropwise thereto in 15 minutes. After 30 minutes of stirring under ice-cooling, this 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 bicarbonate aqueous solution (100 ml) in that order, and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure and the residue was subjected to a silica gel column chromatography. By eluting with a chloroform:methanol of from (50:1) to (20:1), 11.32 g (82%) of the title compound was obtained as a brown oil.

Workup

  1. customAfter evaporation of the solvent under a reduced pressure, toluene (100 ml)
  2. additionwas added
  3. customthe solvent was again evaporated under a reduced pressure
  4. temperaturecooling
  5. stirringstirring
  6. waitin 15 minutes
  7. stirringAfter 30 minutes of stirring under ice-
  8. temperaturecooling
  9. stirringthis was stirred at room temperature for 3 hours
  10. washThe reaction solution was washed with 10% citric acid aqueous solution (100 ml), water (100 ml) and saturated sodium bicarbonate aqueous solution (100 ml) in that order
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was evaporated under a reduced pressure
  13. washBy eluting with a chloroform

Sources & evidence

ORD record
ord-4e1e40eb00a740c5b4d14ccbb4a1c203
Source dataset
uspto-grants-2004_11
Patent number
US06825353B2

Reaction notes

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