Triethylamine → HCID 20741434, compound

HRID 1883958Notes

Reaction equation

HRID 1883958 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

Under ice-cooling, oxalyl chloride (6.54 ml, 0.075 mol) and dimethylformamide (3 drops) were added to dichloromethane solution (200 ml) of 1-[1-(R)-phenylethyl]-5-oxopyrrolidine-3-(R)-carboxylic acid (11.66 g, 0.05 mol) and 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. The residue was mixed with dichloromethane (200 ml) and N,O-methylhydroxylamine hydrochloride (5.47 g, 0.055 mol), and a dichloromethane solution (50 ml) of triethylamine (17.4 ml, 0.125 mol) was added dropwise to the mixture which was stirred under ice-cooling, spending 15 minutes. This was stirred at ice-cooling for 30 minutes and then 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 resulting residue was applied to a silica gel column chromatography. By eluting with a chloroform:methanol system of from (50:1) to (20:1), 11.32 g (82%) of the title compound was obtained as a brown oil.

Workup

  1. temperatureUnder ice-cooling
  2. customAfter evaporation of the solvent under a reduced pressure, toluene (100 ml)
  3. additionwas added
  4. customthe solvent was again evaporated under a reduced pressure
  5. stirringwas stirred under ice-
  6. temperaturecooling
  7. waitspending 15 minutes
  8. stirringThis was stirred at ice-
  9. temperaturecooling for 30 minutes
  10. stirringstirred at room temperature for 3 hours
  11. 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
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe solvent was evaporated under a reduced pressure
  14. washBy eluting with a chloroform

Sources & evidence

ORD record
ord-5f524cd26fc348abb6e69142fb85328d
Source dataset
uspto-grants-2004_07
Patent number
US06762181B1

Reaction notes

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