2,4,5-Trichlorophenol → Benzyloxycarbonyl-D-phenylalanine 2,4,5-trichlorophenyl ester

HRID 256330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 256330
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[CH:26][C:25]=1O.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[CH:26][C:25]=1[O:21][C:20](=[O:22])[C@@H:12]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Komponenten

5

Edukt 3

HCID 72712,4,5-TrichlorophenolHCID 10868DicyclohexylcarbodiimideHCID 675678N-(Benzyloxycarbonyl)-D-phenylalanine

Produkt 1

HCID 14632444Benzyloxycarbonyl-D-phenylalanine 2,4,5-trichlorophenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

60.0 g (0.2 mole) of benzyloxycarbonyl-D-phenylalanine [H. Yajima and K. Kubo: J. Am. Chem. Soc. 87, 2039-2044 (1965)] and 39.4 g (0.2 mole) of 2,4,5-trichlorophenol are dissolved in 200 ml of tetrahydrofuran, the solution is cooled to 5° to 10° C., then at stirring 41.2 g (0.2 mole) of dicyclohexylcarbodiimide are added in about 30 minutes. The reaction mixture is stirred for 6 hours without refrigeration. The precipitated dicyclohexylurea is filtered, washed three times with 50 ml of tetrahydrofuran and the combined tetrahydrofurane solutions are evaporated at reduced pressure. The residue is crystallized from 300 ml of hot etanol, filtered, washed twice with 50 ml of ethanol having a temperature of 5° to 10° C., then the crystals are dried in a vacuum desiccator. Yield: 72 g (75%).

Aufarbeitung

  1. temperaturethe solution is cooled to 5° to 10° C.
  2. additionare added in about 30 minutes
  3. filtrationThe precipitated dicyclohexylurea is filtered
  4. washwashed three times with 50 ml of tetrahydrofuran
  5. customthe combined tetrahydrofurane solutions are evaporated at reduced pressure
  6. customThe residue is crystallized from 300 ml of hot etanol
  7. filtrationfiltered
  8. washwashed twice with 50 ml of ethanol having a temperature of 5° to 10° C.
  9. customthe crystals are dried in a vacuum desiccator

Quellen und Nachweise

ORD-Eintrag
ord-4db6dc43eb604d35946c71886863256e
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04703036

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