Реакция #956977

Уравнение реакции

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

Выход 87.8%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   ДругоеThe resulting reaction mixture
2. 2
   Концентрированиеconcentrated under reduced pressure
3. 3
   workup.ADDITIONThe resulting residue was diluted with EtOAc (50 mL)
4. 4
   Промывкаwashed with brine
5. 5
   Сушкаdried over Na2SO4
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   ДругоеPurification by silica gel chromatography (EtOAc/pentane)

Методика

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%).

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