Sodium Hydroxide → 3-(2,2'-Bisethylcarbamoyl-2-phenylethoxy)propionic acid

HRID 2114184Notes

Reaction equation

HRID 2114184 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][CH2:5][O:6][CH2:7][C:8]([C:20](=[O:24])[NH:21][CH2:22][CH3:23])([C:15](=[O:19])[NH:16][CH2:17][CH3:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>C1COCC1.CO>[CH2:17]([NH:16][C:15]([C:8]([C:20](=[O:24])[NH:21][CH2:22][CH3:23])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:7][O:6][CH2:5][CH2:4][C:3]([OH:25])=[O:2])=[O:19])[CH3:18]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 587063943-(2,2'-Bisethylcarbamoyl-2-phenylethoxy)propionic acid methyl ester

Product 1

HCID 587063833-(2,2'-Bisethylcarbamoyl-2-phenylethoxy)propionic acidYield 95.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(2,2′-Bisethylcarbamoyl-2-phenylethoxy)propionic acid methyl ester (125 mg) was dissolved in THF (0.5 mL) and MeOH (0.5 mL), and 1N sodium hydroxide (0.5 mL) was added thereto. The solution was stirred at room temperature for 1 hour and then concentrated. The residue was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and concentrated to give 3-(2,2′-bisethylcarbamoyl-2-phenylethoxy)propionic acid (115 mg).

Workup

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3ca82c3ad52940c8bf431d4ebb6d5cac
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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