Dicyclohexylcarbodiimide → methyl N-benzoylphenylalanyltyrosinate

HRID 839939Notes

Reaction equation

HRID 839939 reaction equation
[C:1]([NH:9][C@H:10]([C:18]([OH:20])=O)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:22][C@H:23]([C:32]([O:34][CH3:35])=[O:33])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl.O1CCCC1.C(N(CC)CC)C>[C:1]([NH:9][C@H:10]([C:18]([NH:22][C@H:23]([C:32]([O:34][CH3:35])=[O:33])[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=1)=[O:20])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 76956Methyl tyrosinate hydrochlorideHCID 80170N-HydroxysuccinimideHCID 97370Benzoyl-L-phenylalanine

Product 1

HCID 44241224methyl N-benzoylphenylalanyltyrosinateYield 74%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 21956068Chloroform tetrahydrofuranSolvent

Procedure

In 100 ml of a mixture of chloroform-tetrahydrofuran (2:1), were dissolved 5.39 g of N-benzoylphenylalanine, 4.64 g of methyl tyrosinate hydrochloride, 2.02 g of triethylamine and 2.30 g of N-hydroxysuccinimide and the solution was cooled with ice. To the cold solution, 4.12 g of N,N'-dicyclohexylcarbodiimide was added. The mixture was stirred for three hours, then allowed to stand at room temperature overnight. The precipitates were removed by filtration and the filtrate was concentrated. The residue was extracted with ethyl acetate and 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-petroleum ether to give 6.6 g of methyl N-benzoylphenylalanyltyrosinate with a mp. 188°-190° C in a yield of 74%. Analysis, calculated for C26H26O5N2C 69.94, H 5.87, N 6.27, found C 69.56, H 6.01, N 6.39.

Workup

  1. temperaturethe solution was cooled with ice
  2. waitto stand at room temperature overnight
  3. customThe precipitates were removed by filtration
  4. concentrationthe filtrate 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-petroleum ether

Sources & evidence

ORD record
ord-1ce72d1fedcd4fb6930023626eafb32c
Source dataset
uspto-grants-1978_06
Patent number
US04097608

Reaction notes

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