Ethanol → 7-[N-(4-hydroxynonyl)methanesulfonamido]-2-methylheptanoic acid

HRID 372520Notes

Reaction equation

HRID 372520 reaction equation
O1CCCCC1[O:7][CH:8]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:9][CH2:10][CH2:11][N:12]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]([CH3:28])[C:23]([O:25]CC)=[O:24])[S:13]([CH3:16])(=[O:15])=[O:14].C(O)C.[OH-].[Na+]>Cl.O>[OH:7][CH:8]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:9][CH2:10][CH2:11][N:12]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]([CH3:28])[C:23]([OH:25])=[O:24])[S:13]([CH3:16])(=[O:14])=[O:15]

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 20327677ethyl 7-{N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamido}-2-methylheptanoate

Product 1

HCID 203276587-[N-(4-hydroxynonyl)methanesulfonamido]-2-methylheptanoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

A solution is prepared from ethyl 7-{N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamido}-2-methylheptanoate (4.9 g., 0.01 mole), ethanol (50 ml.), and 4 drops of hydrochloric acid (conc.), and kept at ambient temperature for 4.5 hours. Then to the reaction is added a solution of sodium hydroxide (0.72 g., 0.018 mole) in water (10 ml.) and the reaction is kept at ambient temperature for an additional 20 hours. Most of the ethanol is removed in vacuo and the residue dissolved in water (100 ml.). The solution is extracted once with ether (75 ml.) then acidified with hydrochloric acid (dil.). The oil that separates is extracted into ether, the ether is washed with brine, dried over sodium sulfate, then removed under vacuum to give 7-[N-(4-hydroxynonyl)methanesulfonamido]-2-methylheptanoic acid as a yellow liquid.

Workup

  1. waitthe reaction is kept at ambient temperature for an additional 20 hours
  2. customMost of the ethanol is removed in vacuo
  3. dissolutionthe residue dissolved in water (100 ml.)
  4. extractionThe solution is extracted once with ether (75 ml.)
  5. extractionThe oil that separates is extracted into ether
  6. washthe ether is washed with brine
  7. dry with materialdried over sodium sulfate
  8. customremoved under vacuum

Sources & evidence

ORD record
ord-08a3224fda2c4f6ab7e0216b5f4c7640
Source dataset
uspto-grants-1978_05
Patent number
US04091107

Reaction notes

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