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

HRID 1730117Notes

Reaction equation

HRID 1730117 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[O:11]1[CH2:32][CH:12]1[CH2:13][CH2:14][CH2:15][N:16]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[S:17]([CH3:20])(=[O:19])=[O:18].O>CN(C)C=O.C1C=CC=CC=1>[OH:11][CH:12]([CH2:32][O:10][C:7]1[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=1)[CH2:13][CH2:14][CH2:15][N:16]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[S:17]([CH3:20])(=[O:18])=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 21401575ethyl 7-[N-(4,5-epoxypentyl)methanesulfonamido]heptanoate

Product 1

HCID 21401586Ethyl 7-{N-[4-hydroxy-5-(4-fluorophenoxy)pentyl]methanesulfonamido}heptanoate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (57%) (278 mg., 0.0065 mole) in a solvent mixture of benzene (25 ml.) and dimethylformamide (25 ml.) is added, over 30 minutes, a solution of p-fluorophenol (730 mg., 0.065 mole) in dimethylformamide (10 ml.). This mixture is stirred 30 minutes at room temperature, then treated with a solution of ethyl 7-[N-(4,5-epoxypentyl)methanesulfonamido]heptanoate (2.2 g., 0.0065 mole) in benzene (10 ml.). The reaction is heated at 90° C. for eighteen hours, then cooled and poured into water (100 ml.). The organic phase is collected, washed with brine and dried over sodium sulfate. Evaporation in vacuo affords a heavy oil that is purified by chromatography over silica gel, using chloroform to elute. Evaporation of the appropriate fractions affords the subject compound. The yield is 1.4 g. (47%) of heavy oil.

Workup

  1. additionis added, over 30 minutes
  2. temperatureThe reaction is heated at 90° C. for eighteen hours
  3. temperaturecooled
  4. customThe organic phase is collected
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customEvaporation in vacuo
  8. customaffords a heavy oil that
  9. customis purified by chromatography over silica gel
  10. washto elute
  11. customEvaporation of the appropriate fractions
  12. customaffords the subject compound

Sources & evidence

ORD record
ord-59999bb7a1694d1cb7c6c8177bf47f31
Source dataset
uspto-grants-1976_11
Patent number
US03991106

Reaction notes

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