Dimethylformamide → HCID 12547433, compound

HRID 2105292Notes

Reaction equation

HRID 2105292 reaction equation
[C:1]1([S:7]([N:10]2[CH2:17][CH2:16][CH2:15][C@H:11]2[C:12](O)=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:21])=O.CN(C)C=O>ClCCl.C(=O)(O)[O-].[Na+]>[C:1]1([S:7]([N:10]2[CH2:17][CH2:16][CH2:15][CH:11]2[C:12]([Cl:21])=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 720844(2S)-1-(Benzenesulfonyl)pyrrolidine-2-carboxylic acid

Product 1

HCID 12547433HCID 12547433, compoundYield 13.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of the N-phenylsulfonyl proline (1.5 g, 5.8 mmol) in anhydrous dichloromethane (20 mL), were added oxalyl chloride (2.0 M in dichloromethane, 5.9 mL, 11.8 mmol) and a catalytic amount of dimethylformamide. The solution was stirred for 1 hour at room temperature. The reaction mixture was then condensed and diluted with a saturated aqueous solution of sodium bicarbonate (10 mL) and extracted with dichloromethane (20 ml). The organic layers were dried over magnesium sulfate (MgSO4) and filtered and concentrated under reduced pressure to yield 1-benzenesulfonyl-pyrrolidine-2-carbonyl chloride (220 mg) as a yellow solid used without any further purification.

Workup

  1. customcondensed
  2. extractionextracted with dichloromethane (20 ml)
  3. dry with materialThe organic layers were dried over magnesium sulfate (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb9999405951410e937e82571464d993
Source dataset
uspto-grants-2009_08
Patent number
US07579340B2

Reaction notes

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