반응 #1121743

ord-925a704b3637401baa0a658294062243

반응 방정식

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
수율 85.4%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타the mixture was reacted at room temperature for overnight
  2. 2
    기타After completion of the reaction, reaction mixture
  3. 3
    여과was filtered
  4. 4
    추출the filtrate was extracted with ethyl acetate
  5. 5
    농축The extract was concentrated under reduced pressure
  6. 6
    기타the product was crystallized from hexane

실험 절차

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%).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08546072B2uspto-grants-2013_10