Acetic Acid → (2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylic Acid

HRID 496230Notes

Reaction equation

HRID 496230 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:20][CH2:19][CH2:18][C@H:13]2[C:14]([O:16]C)=[O:15])(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+].CC(O)=O>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:20][CH2:19][CH2:18][C@H:13]2[C:14]([OH:16])=[O:15])(=[O:10])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 536917753,5-dichlorophenyl-sulfonyl-L-proline methyl ester

Product 1

HCID 6559079(2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(3,5-dichlorobenzenesulfonyl)-(L)-proline, methyl ester from Step A was dissolved in ethanol (50 mL) and treated with 0.2N sodium hydroxide (26.6 mL) for 1.5 h at rt. The mixture was acidified with glacial HOAc, concentrated by rotoevaporation, and the residue dissolved in CH2Cl2, washed with water, saturated brine solution, dried over anhydrous Na2SO4, and evaporated to give the title compound; yield 1.4 g.

Workup

  1. concentrationconcentrated by rotoevaporation
  2. dissolutionthe residue dissolved in CH2Cl2
  3. washwashed with water, saturated brine solution
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-650f0284cdfe48a8882fe2d6e9a84944
Source dataset
uspto-grants-2005_09
Patent number
US06943180B2

Reaction notes

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