1,2-Dichloroethane → HCID 54284017, compound

HRID 1489165Notes

Reaction equation

HRID 1489165 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:20](O)=[O:21])[CH2:10][C:9](=[O:11])[N:8]([C@@H:12]([CH3:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7]1)=[O:5])[CH3:2].S(Cl)(Cl)=O.Cl[CH2:28][CH2:29]Cl>CN(C)C=O>[CH2:12]([N:8]([CH2:7][C:29]1[CH:28]=[CH:4][CH:6]=[CH:10][CH:9]=1)[C:20]([C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10][C:9](=[O:11])[N:8]([C@@H:12]([CH3:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 24386Thionyl ChlorideHCID 54352233HCID 54352233, compound

Product 1

HCID 54284017HCID 54284017, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

(RS)-3-Ethoxycarbonyl-1-((S)-α-methylbenzyl)-5-oxopyrrolidine-3-carboxylic acid (30.5 g) was dissolved in 1,2-dichloroethane (92 ml), and thionyl chloride (11 ml) and one drop of N,N-dimethylformamide were added. The mixture was refluxed for 2 hours and the reaction mixture was concentrated under reduced pressure. The obtained oil was dissolved in toluene (39 ml) and the mixture was dropwise added to a solution of dibenzylamine (23.7 g) and triethylamine (12.2 g) in toluene (130 ml) under ice-cooling. The mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with water, a sodium hydrogencarbonate-10% aqueous hydrochloric acid solution and water, and dried over anhydrous magnesium sulfate to give the object compound.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe obtained oil was dissolved in toluene (39 ml)
  4. additionthe mixture was dropwise added to a solution of dibenzylamine (23.7 g) and triethylamine (12.2 g) in toluene (130 ml) under ice-
  5. temperaturecooling
  6. washThe reaction mixture was washed with water
  7. dry with materiala sodium hydrogencarbonate-10% aqueous hydrochloric acid solution and water, and dried over anhydrous magnesium sulfate
  8. customto give the object compound

Sources & evidence

ORD record
ord-0df430bf0d664272ae113eae4b8d1ac1
Source dataset
uspto-grants-1997_10
Patent number
US05677316

Reaction notes

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