Water → 7-{N-[4-hydroxy-5-(4-fluorophenoxy)-pentyl]methanesulfonamido}heptanoic acid

HRID 1730118Notes

Reaction equation

HRID 1730118 reaction equation
[OH:1][CH:2]([CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[CH2:3][CH2:4][CH2:5][N:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])[S:7]([CH3:10])(=[O:9])=[O:8].[OH-].[Na+].O>C(O)C>[OH:1][CH:2]([CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[CH2:3][CH2:4][CH2:5][N:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[S:7]([CH3:10])(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21401586Ethyl 7-{N-[4-hydroxy-5-(4-fluorophenoxy)pentyl]methanesulfonamido}heptanoate

Product 1

HCID 214016607-{N-[4-hydroxy-5-(4-fluorophenoxy)-pentyl]methanesulfonamido}heptanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution composed of ethyl 7-{N-[4-hydroxy-5-(4-fluorophenoxy)pentyl]methanesulfonamido}heptanoate (4.7 g., 0.11 mole), sodium hydroxide (1.0 g.), water (13 ml.) and ethanol (130 ml.) is kept at room temperature for 20 hours. Most of the solvent is removed in vacuo, water (150 ml.) is added and the solution extracted with ether (100 ml.). The aqueous layer is acidified (hydrochloric acid) and extracted with ethyl acetate (2 × 100 ml.). The organic layer is dried over sodium sulfate then concentrated in vacuo to obtain the subject compound. The yield is 3.7 g. (84%) of heavy oil.

Workup

  1. customMost of the solvent is removed in vacuo, water (150 ml.)
  2. additionis added
  3. extractionthe solution extracted with ether (100 ml.)
  4. extractionextracted with ethyl acetate (2 × 100 ml.)
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. concentrationthen concentrated in vacuo
  7. customto obtain the subject compound

Sources & evidence

ORD record
ord-dc97aacbc736476bb5e96bd050a1d8aa
Source dataset
uspto-grants-1976_11
Patent number
US03991106

Reaction notes

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