Реакция #1121743

ord-925a704b3637401baa0a658294062243

Уравнение реакции

C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)O
Boc-threonine
CCOC(=O)CN.Cl
glycine ethyl ester hydrochloride
CCN(CC)CC
triethylamine
C(=NC1CCCCC1)=NC1CCCCC1
N,N′-dicyclohexylcarbodiimide
Oc1cccc2[nH]nnc12
hydroxybenzotriazole
CCOC(=O)CNC(=O)[C@@H](NC(=O)OC(C)(C)C)[C@@H](C)O
Boc-Thr-Gly-OEt
Выход 85.4%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Другоеthe mixture was reacted at room temperature for overnight
  2. 2
    ДругоеAfter completion of the reaction, reaction mixture
  3. 3
    Фильтрацияwas filtered
  4. 4
    Экстракцияthe filtrate was extracted with ethyl acetate
  5. 5
    КонцентрированиеThe extract was concentrated under reduced pressure
  6. 6
    Другоеthe product was crystallized from hexane

Методика

Boc-threonine (produced by Wako Pure Chemical Industries Ltd.) (11.0 g, 50 mmol) and glycine ethyl ester hydrochloride (produced by Wako Pure Chemical Industries Ltd.) (8.4 g, 60 mmol) were dissolved in dichloromethane (250 mL). After triethylamine (8.4 mL, 60 mmol), N,N′-dicyclohexylcarbodiimide (DCC, 12.4 g, 60 mmol) and hydroxybenzotriazole (9.2 g, 60 mmol) were further added thereto, the mixture was reacted at room temperature for overnight with stirring. After completion of the reaction, reaction mixture was filtered, and then the filtrate was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the product was crystallized from hexane, to obtain Boc-Thr-Gly-OEt (1) (13.0 g) (yield; 85.1%).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08546072B2uspto-grants-2013_10