Sodium Hydroxide → HCID 18365441, compound

HRID 1953230Notes

Reaction equation

HRID 1953230 reaction equation
C([O:8][C:9]([C:11]1([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1.[OH-].[Na+]>C1COCC1.O.C(OCC)(=O)C>[F:33][C:30]1[CH:31]=[CH:32][C:27]([O:26][C:23]2[CH:24]=[CH:25][C:20]([S:17]([NH:16][C:11]3([C:9]([OH:10])=[O:8])[CH2:15][CH2:14][CH2:13][CH2:12]3)(=[O:18])=[O:19])=[CH:21][CH:22]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 110051711-[4-(4-Fluorophenoxy)benzenesulfonylamino]-cyclopentanecarboxylic acid benzyl ester

Product 1

HCID 18365441HCID 18365441, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[4-(4-Fluoro-phenoxy)-benzenesulfonylamino]-cyclopentanecarboxylic acid benzyl ester (15 g, 32 mmole) in 75 mL THF was combined with 75 mL (150 mmole) 2N aqueous sodium hydroxide and stirred at reflux for 1 hour. The reaction was cooled to ambient temperature and diluted with 100 mL water and 100 mL ethyl acetate. The pH of the aqueous phase was adjusted to pH 1.2 and the ethyl acetate layer separated. The ethyl acetate layer was washed with 100 mL water and dried over magnesium sulfate. The ethyl acetate was stripped in vacuo and replaced with 75 mL methyl tert-butyl ether. The product was filtered and dried to yield 11.16 g (92%) of 1-[4-(4-fluoro-phenoxy) benzenesulfonylamino]-cyclopentanecarboxylic acid. 1H NMR (CDCl3) □ 7.71-7.78 (m, 2H), 6.88-7.04 (m, 6H), 5.04 (s, 1H), 2.01-2.13 (m, 2H), 1.92-1.98 (m, 2H), 1.44-1.68 (m, 4H).

Workup

  1. temperatureat reflux for 1 hour
  2. customthe ethyl acetate layer separated
  3. washThe ethyl acetate layer was washed with 100 mL water
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe product was filtered
  6. customdried

Sources & evidence

ORD record
ord-58672284099f4e29b0024c7743587901
Source dataset
uspto-grants-2000_09
Patent number
US06114568

Reaction notes

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