4-Chlorophenyl Isocyanate → methyl 2-(N'-(4-chlorophenyl)ureido)-3-phenylpropanoate

HRID 1162283Notes

Reaction equation

HRID 1162283 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].C1CCN2C(=NCCC2)CC1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1>C(#N)C>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:35])[NH:6][CH:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([O:3][CH3:2])=[O:14])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 3997616methyl 2-(N'-(4-chlorophenyl)ureido)-3-phenylpropanoateYield 98.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of phenylalanine methyl ester hydrochloride (2.0 g) and DBU (1.4 ml) in acetonitrile (40 ml) was added 4-chlorophenyl isocyanate (1.4 g). The reaction mixture was mixed at room temperature for 1 hour, and then the reaction solution was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as colorless powder (3.0 g, 97%).

Workup

  1. additionThe reaction mixture was mixed at room temperature for 1 hour
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-231b92a6eb894ad28efe00e20040bf4e
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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