Triethylamine → N-benzyloxycarbonyl-L-tryptophan ethyl ester

HRID 1283772

Reaktionsgleichung

Reaktionsgleichung von HRID 1283772
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:23]([OH:25])=[O:24])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26](N(CC)CC)[CH3:27].C(OC(ON=C(C#N)C(OCC)=O)=O)C>C(OCC)(=O)C>[CH2:26]([O:24][C:23](=[O:25])[C@H:12]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH: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])[CH3:27]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 101176benzyloxycarbonyl-L-tryptophanHCID 54447666Ethyl 2-ethoxycarbonyloxyimino-2-cyanoacetate

Produkt 1

HCID 14036692N-benzyloxycarbonyl-L-tryptophan ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-benzyloxycarbonyl-L-tryptophan (1.69 g) and triethylamine (0.70 ml) in ethyl acetate (15 ml), ethyl 2-ethoxycarbonyloxyimino-2-cyanoacetate (1.08 g) is added, and the resulting mixture is stirred at room temperature for 1 hour and allowed to stand over night. The reaction mixture is treated as in Example A whereby crystals are obtained. The crystals are triturated with petroleum ether, and the obtained powder is collected by filtration, dried and recrystallized from an ethyl acetate-petroleum ether mixture to give N-benzyloxycarbonyl-L-tryptophan ethyl ester (1.4 g). M.P. 80 - 83°C.

Aufarbeitung

  1. waitto stand over night
  2. additionThe reaction mixture is treated as in Example A whereby crystals
  3. customare obtained
  4. customThe crystals are triturated with petroleum ether
  5. filtrationthe obtained powder is collected by filtration
  6. customdried
  7. customrecrystallized from an ethyl acetate-petroleum ether mixture

Quellen und Nachweise

ORD-Eintrag
ord-7f32931a2a48463098a161ffad852b05
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03976635

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