Sodium Hydroxide → 1-(4-Fluorobenzenesulfonyl)pyrrolidine-2-carboxylic acid

HRID 1278739Notes

Reaction equation

HRID 1278739 reaction equation
C([O:4][C:5]([CH:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])=[O:6])(C)C.[OH-].[Na+]>CO>[F:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([N:8]2[CH2:9][CH2:10][CH2:11][CH:7]2[C:5]([OH:6])=[O:4])(=[O:14])=[O:13])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 699004021-(4-Fluoro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid isopropyl ester

Product 1

HCID 6150381-(4-Fluorobenzenesulfonyl)pyrrolidine-2-carboxylic acidYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2.06 g (6.5 mmol) of 1-(4-fluoro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid isopropyl ester ( ) in 10 mL of methanol was added 2.3 mL (13 mmol) of 5N NaOH. After 2 hours, the solvent was removed in vacuo and the aqueous residue was acidified with 1N HCl and then extracted twice with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated in vacuo to afford 1.69 g of the title compound as a white solid; ; mp 145-148° C.; 1H NMR (DMSO) δ 1.56-1.63 (m, 1H), 1.78-2.05 (m, 4H), 3.13-3.21 (m, 1H), 4.10-4.15 (m, 1H), 7.42-7.50 (m, 2H), 7.88-7.95 (m, 2H), 12.75 (bs, 1H); MS (ES) m/z 271.9 (MH−); HRMS for C11H12N2FO4S: 274.0543 (MH+).

Workup

  1. customthe solvent was removed in vacuo
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b8778b38d254697b08ec4ed125519e8
Source dataset
uspto-grants-2002_09
Patent number
US06444685B1

Reaction notes

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