反应 #1121743

ord-925a704b3637401baa0a658294062243

反应方程式

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
收率 85.4%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他the mixture was reacted at room temperature for overnight
  2. 2
    其他After completion of the reaction, reaction mixture
  3. 3
    过滤was filtered
  4. 4
    萃取the filtrate was extracted with ethyl acetate
  5. 5
    浓缩The extract was concentrated under reduced pressure
  6. 6
    其他the product was crystallized from hexane

实验过程

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%).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08546072B2uspto-grants-2013_10