Reaktion #84045

Reaktionsgleichung

N-Boc-1,6-diaminohexane

Fmoc-Phe-Gly-OH

N,N′-dicyclohexylcarbodiimide

1-hydroxybenzotriazole hydrate

→

Fmoc-Phe-Gly-NH—(CH2)6NH-Boc

Ausbeute 94.3%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle