Benzoyl chloride → Ethyl Hippurate

HRID 1726377Notes

Reaction equation

HRID 1726377 reaction equation
[NH2:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][NH:1][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:7]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 12176Glycine ethyl ester

Product 1

HCID 226558Ethyl HippurateYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of ethyl 2-amino-acetate (1.0 g, 7.16 mmol) in anhydrous CH2Cl2 (5 ml) was added TEA (1.82 g, 17.96 mmol). The reaction mixture was cooled in an ice bath, and a solution of benzoyl chloride (1.0 g, 7.17 mmol) in CH2Cl2 (2 ml) was added dropwise. After addition was completed, stirring was continued at RT for two more hours. The reaction mixture was washed with water, dried with MgSO4, filtered, and concentrated. Column chromatography (silica, 30% EtOAc in hexanes) gave benzoylaminoacetic acid ethyl ester (intermediate XXa, 1.24 g) as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. additionAfter addition
  3. customwas continued at RT for two more hours
  4. washThe reaction mixture was washed with water
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-24ca47f0b8c34ecd806f091928a42378
Source dataset
uspto-grants-2009_02
Patent number
US07491821B2

Reaction notes

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