Water → HCID 9885481, compound

HRID 258601Notes

Reaction equation

HRID 258601 reaction equation
C([O:4][CH:5]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:6][CH2:7][CH2:8][N:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])[S:10]([CH3:13])(=[O:12])=[O:11])(=O)C.[OH-].[Na+].O>C(O)C>[OH:4][CH:5]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:6][CH2:7][CH2:8][N:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[S:10]([CH3:13])(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 20327690ethyl 7-[N-(4-acetoxynonyl)methanesulfonamido]heptanoate

Product 1

HCID 9885481HCID 9885481, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution composed of ethyl 7-[N-(4-acetoxynonyl)methanesulfonamido]heptanoate (6.0 g., 0.0134 mole), sodium hydroxide (1.66 g., 0.0414 mole), water (9 ml.), and ethanol (81 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 ethyl acetate (100 ml.). Then the aqueous layer is acidified (hydrochloric acid) and extracted again with ethyl acetate (2× 75 ml.). The organic layer is dried over sodium sulfate then concentrated in vacuo to yield 7-[N-(4-hydroxynonyl)methanesulfonamido]heptanoic acid. The yield is 4.3 g. (88%).

Workup

  1. customMost of the solvent is removed in vacuo, water (150 ml.)
  2. additionis added
  3. extractionthe solution extracted with ethyl acetate (100 ml.)
  4. extractionextracted again with ethyl acetate (2× 75 ml.)
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-69381ef298204590b4535479af291c98
Source dataset
uspto-grants-1977_07
Patent number
US04033996

Reaction notes

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