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

HRID 1464217

Reaktionsgleichung

Reaktionsgleichung von HRID 1464217
[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.S(O)(O)(=O)=O.[CH3:24][O:25][C:26](=[O:36])[C@H:27]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH2:28].C(=O)([O-])[O-].[Na+].[Na+].O>C(O)(=O)C>[CH3:24][O:25][C:26](=[O:36])[C@H:27]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH:28][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 10340Sodium CarbonateHCID 11128682(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamateHCID 20841682L-phenylalanine methyl ester sulfate

Produkt 1

HCID 10159630N-(Benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl esterAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

In 100.4 g of acetic acid, 25.1 g (0.1 mole) of N-benzyloxycarbonyl-L-aspartic anhydride was suspended and 27.7 g (0.1 mole) of L-phenylalanine methyl ester sulfate was added at 10°-15° C. Successively 11.1 g (0.105 mole) of sodium carbonate was added at the same temperature. The reaction was carried out for 4 hours with stirring at the same temperature. Thereafter 75.3 g of water was added 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 29.9 g (69.9% yield on L-phenylalanine methyl ester sulfate).

Aufarbeitung

  1. temperaturecooled to 0°-5° C
  2. customPrecipitated crystals
  3. filtrationwere filtered
  4. washwashed
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f708aea14e33496981de38b31f5abfd1
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05302743

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