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p-Anisoyl chloride → methyl N-(4-methoxybenzoyl)phenylalanyltyrosinate

HRID 839941
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 839941
Cl.[NH2:2][C@H:3]([C:11]([NH:13][C@H:14]([C:23]([O:25][CH3:26])=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:33][O:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1>O.C(Cl)(Cl)Cl>[CH3:33][O:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([NH:2][C@H:3]([C:11]([NH:13][C@H:14]([C:23]([O:25][CH3:26])=[O:24])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[O:12])[CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:40])=[CH:37][CH:36]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 7477p-Anisoyl chlorideHCID 10340Sodium Carbonate2×HCID 70615103Methyl phenylalanyltyrosinate hydrochloride

Produkt 1

HCID 53971131methyl N-(4-methoxybenzoyl)phenylalanyltyrosinateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 6212
Chloroform
Lösungsmittel

Versuchsvorschrift

In a mixture of 10 ml of water and 50 ml of chloroform were suspended 3.79 g of methyl phenylalanyltyrosinate hydrochloride and 0.53 g of sodium carbonate. To the mixture was added dropwise 1.75 g of 4-methoxybenzoylchloride in parallel with 10 ml of sodium carbonate solution (0.75 g), while stirring and cooling with ice. The mixture was stirred for two hours and the chloroform layer was collected. The layer was washed with 5% hydrochloric acid and water, dried and concentrated to dryness. The residue was crystallized from ethyl acetate to give 3.9 g of methyl N-(4-methoxybenzoyl)-phenylalanyltyrosinate with a mp. 195°-197° C in a yield of 82%. Analysis, calculated for C27H28O6N2C 68.05, H 5.92, N 5.88, found C 68.42, H 6.08, N 5.74.

Aufarbeitung

  1. temperaturecooling with ice
  2. stirringThe mixture was stirred for two hours
  3. customthe chloroform layer was collected
  4. washThe layer was washed with 5% hydrochloric acid and water
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe residue was crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-60e35d66316d400f8427b127e290cfce
Quelldatensatz
uspto-grants-1978_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04097608

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