Sodium Hydroxide → Y86EH62Njl

HRID 2288107Notes

Reaction equation

HRID 2288107 reaction equation
C([O:3][C:4]([C:6]1([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>O1CCCC1>[F:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][C:19]2[CH:18]=[CH:17][C:16]([S:13]([NH:12][C:6]3([C:4]([OH:5])=[O:3])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]3)(=[O:14])=[O:15])=[CH:21][CH:20]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 544554294-[4-(4-Fluorophenoxy)benzenesulfonylamino]tetrahydropyran-4-carboxylic acid ethyl ester

Product 1

HCID 21868557Y86EH62NjlYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[4-(4-fluorophenoxy)benzenesulfonylamino]tetrahydropyran-4-carboxylic acid ethyl ester (12.1 grams, 0.0286 mole) in tetrahydrofuran (190 mL) was treated with aqueous 3 M sodium hydroxide solution (95 mL, 0.286 mole) and stirred at room temperature for 4 days. The solvent was evaporated under vacuum and the residue partitioned between water and diethyl ether. The aqueous layer was washed with diethyl ether, acidified to pH 1 with 3N aqueous hydrochloric acid solution and extracted with dichloromethane. After washing with water, the organic extract was dried over sodium sulfate, and concentrated to give 4-[4-(4-fluorophenoxy)-benzenesulfonylamino]tetrahydropyran-4-carboxylic acid (11.241 grams, 99%) as a yellowish solid foam.

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue partitioned between water and diethyl ether
  3. washThe aqueous layer was washed with diethyl ether
  4. extractionextracted with dichloromethane
  5. washAfter washing with water
  6. extractionthe organic extract
  7. dry with materialwas dried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8372c288608746aab3d2bf3d725026b0
Source dataset
uspto-grants-2000_07
Patent number
US06087392

Reaction notes

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