Water → 4-(2-(11-Carboxyundecanoylamino)phenoxy)-butyric acid

HRID 1290709Notes

Reaction equation

HRID 1290709 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:17][C:18]1[CH:32]=[CH:31][CH:30]=[CH:29][C:19]=1[O:20][CH2:21][CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[O:16])([O:3]C)=[O:2].O.[OH-].[Na+]>CO>[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:17][C:18]1[CH:32]=[CH:31][CH:30]=[CH:29][C:19]=1[O:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:16])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 18796179Ethyl 4-(2-(11-carbomethoxyundecanoylamino)phenoxy)butyrate

Product 1

HCID 187958444-(2-(11-Carboxyundecanoylamino)phenoxy)-butyric acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (8) (1.0 g, 2.22 mM) in methanol (100 mL) is added 1 mL of water followed by dropwise addition of 2.5N sodium hydroxide solution (4.0 mL). The walls of the reaction flask are rinsed down with 10 mL of methanol and the mixture is stirred under a nitrogen atmosphere until TLC analysis shows no ester (mono- or di-) remaining. The methanol is removed in vacuo, the residue taken up in 100 mL of water, stirred for solution, filtered (20 mL water rinses), and the stirred filtrate acidified dropwise with 2N hydrochloric acid. Filtration of the resultant precipitate followed by copious water washing and drying gave 0.87 g (96%) of (9) as a chalk-like white solid. The compound was one component by TLC (silica gel, the eluant was 10 mL of 2% methanol in methylene chloride containing 4 drops of glacial acetic acid). mp 128.5°-130° C. uncorr.

Workup

  1. washThe walls of the reaction flask are rinsed down with 10 mL of methanol
  2. customThe methanol is removed in vacuo
  3. stirringstirred for solution
  4. filtrationfiltered (20 mL water rinses)
  5. filtrationFiltration of the resultant precipitate
  6. customdrying

Sources & evidence

ORD record
ord-4c3255e8d3d84c2ea168065631603587
Source dataset
uspto-grants-1998_05
Patent number
US05753641

Reaction notes

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