Water → N-(Benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester

HRID 1464215

Reaktionsgleichung

Reaktionsgleichung von HRID 1464215
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:17](=[O:18])[O:16][C:14](=[O:15])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].Cl.[CH3:25][O:26][C:27](=[O:37])[C@H:28]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH2:29].O>C(O)(=O)C>[CH3:25][O:26][C:27](=[O:37])[C@H:28]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH:29][C:17](=[O:18])[C@H:12]([CH2:13][C:14](=[O:15])[OH:16])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Komponenten

6

Edukt 4

HCID 962WaterHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 517045Sodium AcetateHCID 11128682(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate

Produkt 1

HCID 10159630N-(Benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl esterAusbeute 68,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

In 75.3 g of acetic acid, 25.1 g (0.1 mole) of N-benzyloxycarbonyl-L-aspartic anhydride was suspended and 9.2 g (0.11 mole) of sodium acetate was added at 20°-25° C. with stirring. After cooling to 15°-20° C., 64.8 g of an acetic acid solution containing 21.6 g (0.1 mole) of L-phenylalanine methyl ester hydrochloride was added at the same temperature. The reaction was carried out for 2 hours with stirring at the same temperature. Thereafter 110.1 g of water was added at the same temperature and cooled to 0°-5° C. Precipitated crystals were filtered, washed and dried. Crystals of N-benzyloxycarbonyl-α-L-aspartyl-L-phenylalanine methyl ester were obtained. The yield was 29.5 g (68.9% yield on L-phenylalanine methyl ester hydrochloride).

Aufarbeitung

  1. temperatureAfter cooling to 15°-20° C.
  2. additionwas added at the same temperature
  3. stirringwith stirring at the same temperature
  4. temperaturecooled to 0°-5° C
  5. customPrecipitated crystals
  6. filtrationwere filtered
  7. washwashed
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d4aad907d2f04853b5823bdf25c252d7
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05302743

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