Réaction #51479

Équation de réaction

2-[(2-cyanoethyl)(dimethylethoxycarbonyl)amino]acetic acid

carbonyldiimidazole

homopiperonylamine, hydrochloride

diisopropylethylamine

→

2-[(2-cyanoethyl)(dimethylethoxycarbonyl)amino]-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamide

Rendement 88.8%

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGAfter stirring for 18 hours, most of the solvent
2. 2
   Autrewas removed in vacuo
3. 3
   Autrethe residue was partitioned with ethyl acetate and 1N HCl
4. 4
   AutreThe organic layer was separated
5. 5
   Lavagewashed with aqueous bicarbonate and brine
6. 6
   Séchagedried (Na2SO4)
7. 7
   Autrethe solvent was removed in vacuo

Mode opératoire

In a manner similar to the preparation of compounds of formula (Yc3) above, to 2-[(2-cyanoethyl)(dimethylethoxycarbonyl)amino]acetic acid (8.3 g, 39 mmol) dissolved in CH2Cl2 (100 mL) was added carbonyldiimidazole (6.2 g, 38 mmol). After stirring for 30 minutes, homopiperonylamine, hydrochloride (8.0 g, 41 mmol) and diisopropylethylamine (7.5 mL, 43 mmol) were added. After stirring for 18 hours, most of the solvent was removed in vacuo and the residue was partitioned with ethyl acetate and 1N HCl. The organic layer was separated, washed with aqueous bicarbonate and brine, dried (Na2SO4), and the solvent was removed in vacuo to give 13 g of 2-[(2-cyanoethyl)(dimethylethoxycarbonyl)amino]-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamide.

Source