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

HRID 351683Notes

Reaction equation

HRID 351683 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-d5d623fd3b174366bc097b735d11d57d
Source dataset
uspto-grants-2004_06
Patent number
US06743787B2

Reaction notes

Loading…