반응 #1531339

반응 방정식

HOBt

H2O

HBTU

Et3N

TFA

Boc-L-Ile-D-Pro-OBzl

Boc-D-Tyr(Me)-OH

→

desired product

Boc-D-Tyr(Me)-L-Ile-D-Pro-OBzl

반응 조건

후처리

1. 1
   workup.WAITthis was left
2. 2
   기타TFA was removed by evaporation
3. 3
   기타the residue was dried under reduced pressure
4. 4
   workup.DISSOLUTIONThis was dissolved in DMF (8 mL)
5. 5
   농축The reaction solution was concentrated
6. 6
   추출extracted with ethyl acetate
7. 7
   세척the extract was washed 3 times each with 10% aqueous citric acid solution, 4% aqueous sodium bicarbonate solution, and saturated bee
8. 8
   건조dried over magnesium sulfate
9. 9
   기타ethyl acetate was removed by evaporation
10. 10
    기타Purification by silica gel chromatography

실험 절차

While cooling on ice, TFA (5 mL) was added to Boc-L-Ile-D-Pro-OBzl (1.63 g, 3.38 mmol), and this was left to stand for 30 minutes. TFA was removed by evaporation, and the residue was dried under reduced pressure. This was dissolved in DMF (8 mL), Boc-D-Tyr(Me)-OH (1.50 g, 5.07 mmol) was added, and while cooling on ice, HOBt.H2O (518 mg, 3.38 mmol), HBTU (1.92 g, 5.07 mmol), and Et3N (2.37 ml, 16.9 mmol) were added, and this mixture was stirred for 3 hours. The reaction solution was concentrated, extracted with ethyl acetate, the extract was washed 3 times each with 10% aqueous citric acid solution, 4% aqueous sodium bicarbonate solution, and saturated bee, and dried over magnesium sulfate, and then ethyl acetate was removed by evaporation. Purification by silica gel chromatography yielded the desired product as a foam (column: Merck Kieselgel 60 Φ 3.4×30 cm, eluent: CHCl3/MeOH, 99/1). TLC: Rf, 0.89 (CHCl3/MeOH, 9/1). Yield: 1.44 g (2.42 mmol, 72%).

출처