Reacción #313369

Ecuación de reacción

Benzenesulfonyl chloride

methyl 6-aminohexanoate hydrochloride

sodium carbonate

→

title compound

6-Benzenesulfonylaminohexanoic acid methyl ester

Disolventes

acetonitrile

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe product was extracted with ethyl acetate (30 ml)
2. 2
   SecadoThe extract was dried (Na2SO4) and solvents
3. 3
   Otrowere removed under reduced pressure
4. 4
   OtroThe product was chromatographed on silica gel with ethyl acetate-hexane (1:2) as eluent

Procedimiento

Benzenesulfonyl chloride (92a) (0.88 g, 5.0 mmol) was added to the mixture of methyl 6-aminohexanoate hydrochloride (91) (1.82 g, 10 mmol) in acetonitrile (10 ml) and sodium carbonate (2.6 g, 24.6 mmol) in water (10 ml). The mixture was stirred for 6 hours at ambient temperature, and the product was extracted with ethyl acetate (30 ml). The extract was dried (Na2SO4) and solvents were removed under reduced pressure. The product was chromatographed on silica gel with ethyl acetate-hexane (1:2) as eluent. The title compound was obtained as oil (128 g, 90%). 1H NMR δH (90 MHz, DMSO-d6) δ: 0.90-1.63 (6H, m, CH2); 2.21 (2H, t, J=7.0 Hz, CH2); 2.71 (2H, q, J=6.0 Hz, CH2N); 3.58 (3H, s, CH3); 7.40-7.72 (3H, m, C6H3); 7.72-7.89 (2H, m, C6H2).

Fuente