1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 131723563, compound

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Reaction Steps

In a 100 ml round bottom flask, 0.50 mmol of Boc-Aib (Aib=α-aminoisobutyric acid) was dissolved in 30 ml dry CH2Cl2 and then 0.51 mmol of 1-hydroxybenzotrizole was added while stirring under N2 atmosphere in an ice-bath, 0.55 mmol of 1-ethyl-3-(3′-dimethylaminopropyl) carbodiimide HCl was added in 20 ml dry CH2Cl2 at a fast drop rate and the reaction was stirred for 1 hour at 0° C. 0.51 mmol of (2) in 15 ml of CH2Cl2 was added dropwise and stirring was continued for a further 18 h at ambient temperature. The reaction mixture was washed with 20 ml of 20% citric acid aqueous solution, 20 ml of saturated NaCHO3 aqueous solution, and 20 ml of saturated sodium chloride aqueous solution. The organic layer was separated and dried over anhydrous magnesium sulfate, filtered and concentrated in vacuum. Further purification was done by flash column chromatography (CHCl3/MeOH, 95:5) to afford white solid of Boc-Aib-DTrp-DPro-diisobutylamide.

Provenance & Evidence