Tetrahydrofuran → HCID 23138257, compound

HRID 1162289Notes

Reaction equation

HRID 1162289 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:24])[NH:10][CH2:11][CH:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]([O:15]CC)=[O:14])=[CH:4][CH:3]=1.[OH-].[Na+].C1COCC1>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:24])[NH:10][CH2:11][CH:12]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:13]([OH:15])=[O:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23138304HCID 23138304, compound

Product 1

HCID 23138257HCID 23138257, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-(N′-(4-chlorophenyl)ureido)-2-phenylpropanoate (1.5 g) obtained in Example 4a) and 1 N sodium hydroxide (10 ml) in ethanol (20 ml)-THF (20 ml) was mixed at room temperature for 15 hours, and then 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 (1.4 g, quantitative).

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-442289b1402d4f7fb33f7200a5bf4111
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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