Реакция #84045

Уравнение реакции

N-Boc-1,6-diaminohexane

Fmoc-Phe-Gly-OH

N,N′-dicyclohexylcarbodiimide

1-hydroxybenzotriazole hydrate

→

Fmoc-Phe-Gly-NH—(CH2)6NH-Boc

Выход 94.3%

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred overnight
2. 2
   ФильтрацияSolids were filtered off
3. 3
   Промывкаthey were washed with EtOAc
4. 4
   КонцентрированиеThe filtrate and washings were then concentrated under reduced pressure
5. 5
   ДругоеThe resulting residue was purified by flash column chromatography (0 to 10% MeOH in CH2Cl2)

Методика

To a solution of Fmoc-Phe-Gly-OH (0.66 g) in anhydrous THF (20 mL) at 0° C. under N2 was added N,N′-dicyclohexylcarbodiimide (0.307 g) and 1-hydroxybenzotriazole hydrate (0.201 g). After stirring for 15 min, N-Boc-1,6-diaminohexane (0.322 g) was added. The reaction mixture was allowed to warm to RT and stirred overnight. Solids were filtered off and they were washed with EtOAc. The filtrate and washings were then concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (0 to 10% MeOH in CH2Cl2) to afford Fmoc-Phe-Gly-NH—(CH2)6NH-Boc as a white solid (0.9 g).

Источник