Dicyclohexylcarbodiimide → methyl N-(4-methoxybenzoyl)phenylalanyltyrosinate

HRID 839940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 839940
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21956068Chloroform tetrahydrofuranLösungsmittel

Versuchsvorschrift

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 two hours and then allowed to sit at room temperature overnight. The precipitates were removed by filtration and the filtrate 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.

Aufarbeitung

  1. temperaturethe mixture was cooled with ice
  2. waitto sit 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

Quellen und Nachweise

ORD-Eintrag
ord-c5f90aff96014f3aac2bc5a7d9113144
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04097608

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