반응 #956977

반응 방정식

HATU

(S)-tert-butyl 6-amino-2-((2-(trimethylsilyl)ethoxy)carbonyl)hexanoate

monomethyl fumarate

DIEA

→

(S,E)-tert-butyl 6-(4-methoxy-4-oxobut-2-enamido)-2-((2-(trimethylsilyl)ethoxy)carbonyl)hexanoate

수율 87.8%

용매

acetonitrile

반응 조건

후처리

1. 1
   기타The resulting reaction mixture
2. 2
   농축concentrated under reduced pressure
3. 3
   workup.ADDITIONThe resulting residue was diluted with EtOAc (50 mL)
4. 4
   세척washed with brine
5. 5
   건조dried over Na2SO4
6. 6
   농축concentrated under reduced pressure
7. 7
   기타Purification by silica gel chromatography (EtOAc/pentane)

실험 절차

To a stirring mixture of (S)-tert-butyl 6-amino-2-((2-(trimethylsilyl)ethoxy)carbonyl)hexanoate (800 mg, 2.31 mmol), monomethyl fumarate (361 mg, 2.77 mmol), DIEA (1.1 mL, 6.93 mmol) in 10 mL acetonitrile was added HATU (1.14 g, 3.00 mmol) in one portion at 0° C. under an inert atmosphere of argon. The resulting reaction mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The resulting residue was diluted with EtOAc (50 mL) and washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Purification by silica gel chromatography (EtOAc/pentane) afforded (S,E)-tert-butyl 6-(4-methoxy-4-oxobut-2-enamido)-2-((2-(trimethylsilyl)ethoxy)carbonyl)hexanoate (900 mg, 85%).

출처