Reacción #1449734

Ecuación de reacción

(2E,4E)-5-(2-nitrophenyl)penta-2,4-dienoic acid

tetrahydrofuran

triethylamine

methyl 6-aminohexanoate hydrochloride

→

title compound

Rendimiento 89.5%

(2E,4E)-6-[5-(2-Nitrophenyl)penta-2,4-dienoylamino]hexanoic acid methyl ester

Rendimiento 89.5%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was evaporated, to the obtained residue water (15 ml)
2. 2
   workup.ADDITIONwas added
3. 3
   Filtraciónthe precipitate was filtered off
4. 4
   LavadoThe precipitate was washed with an additional amount of water
5. 5
   Otrodried

Procedimiento

To a solution of (2E,4E)-5-(2-nitrophenyl)penta-2,4-dienoic acid (9a) (0.44 g, 2.0 mmol) in dry tetrahydrofuran (10 ml) 1,1′-carbonyldiimidazole (0.36 g, 2.2 mmol) (Sigma-Aldrich) was added and the mixture was stirred for 1 hour at ambient temperature. To the reaction mixture triethylamine (0.30 g 3.0 mmol) and methyl 6-aminohexanoate hydrochloride (10) (0.40 g, 2.2 mmol) successively were added and the resultant suspension was stirred for 6 hour at ambient temperature. The solvent was evaporated, to the obtained residue water (15 ml) was added and the precipitate was filtered off. The precipitate was washed with an additional amount of water and dried to give the title compound (0.62 g, 89%) as a yellow solid, m.p. 115-117° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.10-1.79 (6H, m, CH2); 2.29 (2H, J=7.0 Hz, CH2); 3.17 (2H, q, J=5.6 Hz, CH2N); 3.60 (3H, s); 6.24 (1H, d, J=14.8 Hz, CH); 7.04-8.10 (8H, m, CH—CH═CH, C6H4, NH).

Fuente