Reaktion #345783

ord-69381ef298204590b4535479af291c98

Reaktionsgleichung

CCCCCC(CCCN(CCCCCCC(=O)OCC)S(C)(=O)=O)OC(C)=O
ethyl 7-[N-(4-acetoxynonyl)methanesulfonamido]heptanoate
[Na+].[OH-]
sodium hydroxide
O
water
→
CCCCCC(O)CCCN(CCCCCCC(=O)O)S(C)(=O)=O
7-[N-(4-hydroxynonyl)methanesulfonamido]heptanoic acid

Edukte

CCCCCC(CCCN(CCCCCCC(=O)OCC)S(C)(=O)=O)OC(C)=O
ethyl 7-[N-(4-acetoxynonyl)methanesulfonamido]heptanoate
[Na+].[OH-]
sodium hydroxide
O
water

Reagenzien

Keine

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeMost of the solvent is removed in vacuo, water (150 ml.)
  2. 2
    workup.ADDITIONis added
  3. 3
    Extraktionthe solution extracted with ethyl acetate (100 ml.)
  4. 4
    Extraktionextracted again with ethyl acetate (2× 75 ml.)
  5. 5
    TrocknenThe organic layer is dried over sodium sulfate
  6. 6
    Einengenthen concentrated in vacuo

Vorschrift

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%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04033996uspto-grants-1977_07