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

HRID 234713Notes

Reaction equation

HRID 234713 reaction equation
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

Participants

5

Reactant 2

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

Product 1

HCID 15230237(1-Dibenzylaminocarbonyl-1,2,3,4-tetrahydronaphthalen-5-yl)oxyacetic acidYield 86.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3a0c3e53415645eba0254c2e93098166
Source dataset
uspto-grants-1997_01
Patent number
US05596009

Reaction notes

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