Dicyclohexylcarbodiimide → N-(N-acetylphenylglycyl)phenylglycine methyl ester

HRID 231387

Reaction equation

HRID 231387 reaction equation
[C:1]([N:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:5][C:6](O)=[O:7])(=[O:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[CH3:30][O:31][C:32](=[O:41])[CH2:33][NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)(Cl)Cl>[CH3:30][O:31][C:32](=[O:41])[CH2:33][N:34]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:6](=[O:7])[CH2:5][N:4]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 68483Glycine, N-acetyl-N-phenyl-HCID 571509Methyl 2-(phenylamino)acetate

Product 1

HCID 54490523N-(N-acetylphenylglycyl)phenylglycine methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 20 parts by volume of chloroform was added 0.96 part by weight of N-acetylphenylglycine. With ice cooling, 1.03 parts by weight of dicyclohexylcarbodiimide was added, and the mixture was stirred. Furthermore, 0.83 part by weight of phenylglycine methyl ester was added, and about 3 hours later, the temperature was returned to room temperature. The mixture was then stirred overnight. After the reaction, the precipitate was collected by filtration, and washed with chloroform. The filtrate was concentrated to dryness. The resulting solid was washed with ethyl acetate, and extracted with a mixture of chloroform and petroleum ether to give 1.2 parts by weight of the captioned compound having a melting point of 198° to 200°C.

Workup

  1. customabout 3 hours
  2. customwas returned to room temperature
  3. stirringThe mixture was then stirred overnight
  4. customAfter the reaction
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with chloroform
  7. concentrationThe filtrate was concentrated to dryness
  8. washThe resulting solid was washed with ethyl acetate
  9. extractionextracted with a mixture of chloroform and petroleum ether
  10. customto give 1.2 parts by weight of the captioned compound

Sources & evidence

ORD record
ord-568224f76f9c47dda0b975f9bae625b0
Source dataset
uspto-grants-1989_07
Patent number
US04846877

Linked notes

Loading…