Reacción #84045

Ecuación de reacción

N-Boc-1,6-diaminohexane

Fmoc-Phe-Gly-OH

N,N′-dicyclohexylcarbodiimide

1-hydroxybenzotriazole hydrate

→

Fmoc-Phe-Gly-NH—(CH2)6NH-Boc

Rendimiento 94.3%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente