Реакция #575823

Уравнение реакции

N-acetyl-4-{2-[(benzhydryloxy)carbonyl][tert-butoxy(oxo)acetyl]anilino}-3-ethylphenylalanine

2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate

diisopropylethylamine

2-(trimethylsilyl)ethyl 5-[(tert-butoxycarbonyl)amino]pentanoate

HCl

→

titled compound

Выход 55.5%

benzhydryl 2-{4-[2-(acetylamino)-3-oxo-3-({5-oxo-5-[2-(trimethylsilyl)ethoxy]pentyl}amino)propyl][tert-butoxy(oxo)acetyl]-2-ethylanilino}benzoate

Выход 55.5%

Растворители

N,N-dimethylformamide

dioxane

ethyl acetate

Условия реакции

Обработка

1. 1
   Концентрированиеconcentrated under reduced pressure
2. 2
   Промывкаwashed with aqueous NaHCO3 (1×30 mL), brine (1×30 mL)
3. 3
   Сушкаdried (MgSO4)
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrate under reduced pressure
6. 6
   ДругоеThe residue was purified on silica gel eluting with ethyl acetate

Методика

2-(trimethylsilyl)ethyl 5-[(tert-butoxycarbonyl)amino]pentanoate (317 mg, 1.0 mmol) was treated with 4N HCl in dioxane at room temperature for 30 minutes, then concentrated under reduced pressure. The residue (665 mg, 1.0 mmol), N-acetyl-4-{2-[(benzhydryloxy)carbonyl][tert-butoxy(oxo)acetyl]anilino}-3-ethylphenylalanine (665 mg, 1.0 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (321 mg, 1.0 mmol) and diisopropylethylamine (521 μL, 3.0 mmol) in N,N-dimethylformamide (2 mL) was stirred at ambient temperature overnight, diluted with ethyl acetate and washed with aqueous NaHCO3 (1×30 mL), brine (1×30 mL), dried (MgSO4), filtered and concentrate under reduced pressure. The residue was purified on silica gel eluting with ethyl acetate to provide of titled compound 480 mg. MS (APCI(+)) m/e 864 (M+H)+.

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