Tetrahydrofuran → 2-(N'-(4-chlorophenyl)ureido)-3-phenylpropanoic acid

HRID 1162284Notes

Reaction equation

HRID 1162284 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:23])[NH:10][CH:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([O:14]C)=[O:13])=[CH:4][CH:3]=1.[OH-].[Na+].C1COCC1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:23])[NH:10][CH:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([OH:14])=[O:13])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 3997616methyl 2-(N'-(4-chlorophenyl)ureido)-3-phenylpropanoate

Product 1

HCID 29747892-(N'-(4-chlorophenyl)ureido)-3-phenylpropanoic acidYield 96.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-(N′-(4-chlorophenyl)ureido)-3-phenylpropanoate (2.8 g) obtained in Example 1a) and 1 N sodium hydroxide (20 ml) in methanol (20 ml)-THF (10 ml) was mixed at room temperature for 15 hours, and the reaction solution was concentrated under reduced pressure. The solution was acidified by adding 1 N hydrochloric acid to the concentrated solution, and then extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as colorless powder (2.6 g, 95%).

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. additionby adding 1 N hydrochloric acid to the concentrated solution
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2942acb980cd4ee7b607d0cb19937bbc
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

Loading…