Reaction #84045

Reaction equation

N-Boc-1,6-diaminohexane

Fmoc-Phe-Gly-OH

N,N′-dicyclohexylcarbodiimide

1-hydroxybenzotriazole hydrate

→

Fmoc-Phe-Gly-NH—(CH2)6NH-Boc

Yield 94.3%

Solvents

THF

Conditions

Workup

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

Procedure

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).

Source