Sodium Hydroxide → (1-Dibenzylaminocarbonyl-1,2,3,4-tetrahydronaphthalen-5-yl)oxyacetic acid

HRID 234713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 234713
C[O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][CH:11]2[C:16]([N:18]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].[OH-].[Na+]>C(COC)OC.CO>[CH2:26]([N:18]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:16]([CH:11]1[C:12]2[C:7](=[C:6]([O:5][CH2:4][C:3]([OH:33])=[O:2])[CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:9][CH2:10]1)=[O:17])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 15230236Methyl(1-dibenzylaminocarbonyl-1,2,3,4-tetrahydronaphthalen-5-yl)oxyacetate

Produkt 1

HCID 15230237(1-Dibenzylaminocarbonyl-1,2,3,4-tetrahydronaphthalen-5-yl)oxyacetic acidAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a solution of the compound prepared in example 1 (204 mg) in dimethoxyethane (3 ml) and methanol (2 ml) was added 1N aqueous solution of sodium hydroxide. After stirred for 2 h, the mixture was quenched by addition of 1N hydrochloric acid. The mixture was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium salfate, and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4→ethyl acetate) to give the title compound (171 mg) having the following physical data.

Aufarbeitung

  1. customthe mixture was quenched by addition of 1N hydrochloric acid
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium salfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4→ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3a0c3e53415645eba0254c2e93098166
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05596009

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