Dicyclohexylcarbodiimide → methyl N-(4-methoxybenzoyl)phenylalanyltyrosinate

HRID 1439006Notes

Reaction equation

HRID 1439006 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:9][C@H:10]([C:18]([OH:20])=O)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:8])=[CH:5][CH:4]=1.Cl.[NH2:24][C@H:25]([C:34]([O:36][CH3:37])=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C@H:10]([C:18]([NH:24][C@H:25]([C:34]([O:36][CH3:37])=[O:35])[CH2:26][C:27]2[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=2)=[O:20])[CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:8])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 76956Methyl tyrosinate hydrochlorideHCID 919358N-(4-methoxybenzoyl)-phenylalanine

Product 1

HCID 53971131methyl N-(4-methoxybenzoyl)phenylalanyltyrosinateYield 74%

Reagents, catalysts & solvents 1

HCID 21956068Chloroform tetrahydrofuranSolvent

Procedure

In 500 ml of a mixture of chloroform-tetrahydrofuran (2:1), were dissolved 29.9 g of N-(4-methoxybenzoyl)-phenylalanine, 23.2 g of methyl tyrosinate hydrochloride, 10.1 g of trethylamine and 11.6 g of H-hydroxysuccinimide and the mixture was cooled with ice. To the cold solution was added 20.6 g of N,N'-dicyclohexylcarbodiimide. The mixture was stirred for 2 hours and then allowed to sit at room temperature overnight. The precipitates were removed by filtration and the filtrte was concentrated. The residue was extracted with ethyl acetate. The extract was washed with 2% hydrochloric acid, 4% sodium bicarbonate and water, then dried and concentrated to dryness. The residue was crystallized from ethyl acetate to give 35 g of methyl N-(4-methoxybenzoyl)phenylalanyltyrosinate with a mp. 195°-197° C in a yield of 74%. Analysis, calculated for C27H28O6N2C 68.05, H 5.92, N 5.88, found C 67.84, H 5.92, N 5.57.

Workup

  1. temperaturethe mixture was cooled with ice
  2. waitto sit at room temperature overnight
  3. customThe precipitates were removed by filtration
  4. concentrationthe filtrte was concentrated
  5. extractionThe residue was extracted with ethyl acetate
  6. washThe extract was washed with 2% hydrochloric acid, 4% sodium bicarbonate and water
  7. customdried
  8. concentrationconcentrated to dryness
  9. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-46d92a82dce641f5af4aa4026c30d07a
Source dataset
uspto-grants-1977_11
Patent number
US04057629

Reaction notes

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