Reaktion #1121743

ord-925a704b3637401baa0a658294062243

Reaktionsgleichung

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
Ausbeute 85.4%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe mixture was reacted at room temperature for overnight
  2. 2
    SonstigeAfter completion of the reaction, reaction mixture
  3. 3
    Filtrationwas filtered
  4. 4
    Extraktionthe filtrate was extracted with ethyl acetate
  5. 5
    EinengenThe extract was concentrated under reduced pressure
  6. 6
    Sonstigethe product was crystallized from hexane

Vorschrift

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%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08546072B2uspto-grants-2013_10