Sodium Hydroxide → Y86EH62Njl

HRID 2288108Notes

Reaction equation

HRID 2288108 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+]>C(O)C>[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 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-[4-(4-fluorophenoxy)benzenesulfonylamino]tetrahydropyran-4-carboxylic acid ethyl ester (34.19 grams, 0.807 mole) in ethanol (330 mL) was treated with aqueous 3 M sodium hydroxide solution (330 mL, 0.990 mole) and heated to reflux overnight. 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 ethyl acetate. After washing with water, the organic extract was dried over sodium soulfate, and concentrated to give 4-[4-(4-fluorophenoxy)benzenesulfonylamino]tetrahydropyran-4-carboxylic acid (31.26 grams, 98%) as a white crystalline solid. 1HNMR (CDCl3) δ 7.73 (d, 2H), 7.03 (t, 2H) 6.96 (m, 2H), 6.91 (d, 2H), 3.56 (m, 2H), 3.43 (br m, 3H), 2.01 (m, 2H), 1.80 (br d, 2H). MS Atmospheric Pressure Chemical Ionization Mass Spectra: 394 (M+ -1) (-ion).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe solvent was evaporated under vacuum
  4. customthe residue partitioned between water and diethyl ether
  5. washThe aqueous layer was washed with diethyl ether
  6. extractionextracted with ethyl acetate
  7. washAfter washing with water
  8. extractionthe organic extract
  9. dry with materialwas dried over sodium soulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f5412b50b5e245b68328dbc71c24b776
Source dataset
uspto-grants-2000_07
Patent number
US06087392

Reaction notes

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