Lithium Hydroxide → 2-(1-(3,4-Dichlorophenylsulfonyl)pyrrolidin-2-yl)acetic acid

HRID 1642144Notes

Reaction equation

HRID 1642144 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[CH:5]=[C:6]([S:11]([N:14]2[CH2:18][CH2:17][CH2:16][CH:15]2[CH2:19][C:20]([O:22]C)=[O:21])(=[O:13])=[O:12])[CH:7]=[CH:8][C:9]=1[Cl:10]>CO.O>[Cl:3][C:4]1[CH:5]=[C:6]([S:11]([N:14]2[CH2:18][CH2:17][CH2:16][CH:15]2[CH2:19][C:20]([OH:22])=[O:21])(=[O:12])=[O:13])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66756029HCID 66756029, compound

Product 1

HCID 613720752-(1-(3,4-Dichlorophenylsulfonyl)pyrrolidin-2-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide (0.75 mg, 18 mmol) was added to a cooled solution of methyl 2-(1-(3,4-dichlorophenylsulfonyl)pyrrolidin-2-yl)acetate (2.1 g, 6 mmol) in methanol (20 ml) and water (20 ml), and stirring was carried out for 16 h at room temperature (TLC monitoring). The solvent was removed using a rotary evaporator and the residue was taken up in water. The aqueous phase was washed with ethyl acetate and acidified with 1 M HCl, and then the product was extracted with ethyl acetate and the organic phase was washed with saturated NaCl solution. The organic phase was dried over sodium sulfate and concentrated to dryness. Yield: 2.0 g (99%)

Workup

  1. customThe solvent was removed
  2. customa rotary evaporator
  3. washThe aqueous phase was washed with ethyl acetate
  4. extractionthe product was extracted with ethyl acetate
  5. washthe organic phase was washed with saturated NaCl solution
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-19777be39ab64f078254da7741e91b82
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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