Reacción #1694949

Ecuación de reacción

triethylamine

N-methylglycine methyl ester hydrochloride

oxalyl chloride

2,6-dimethoxy-1-naphthalenecarboxylic acid

→

title compound

Rendimiento 79.7%

N-[(2,6-Dimethoxy-1-naphthalenyl)carbonyl]-N-methylglycine Methyl Ester

Rendimiento 79.7%

Disolventes

CH2Cl2

water

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe aqueous phase was washed with CH2Cl2 (100 mL)
2. 2
   Lavadothe combined CH2Cl2 phases were washed successively with 1M H3PO4 (2 x 100 mL), water (100 mL), saturated NaHCO3 (50 mL), brine (100 mL)
3. 3
   Secadodried over Na2SO4
4. 4
   FiltraciónFiltration and concentration
5. 5
   workup.WAITleft a pale brown foam which
6. 6
   Filtraciónwas filtered through a short column of silica gel with 1:1 ethyl acetate

Procedimiento

A solution of oxalyl chloride (0.95 mL, 11 mmol) in CH2Cl2 (10 mL) was added to a suspension of 2,6-dimethoxy-1-naphthalenecarboxylic acid (2.32 g, 10 mmol, described in Example 1) and N,N-dimethylformamide (2 drops, catalyst) in CH2Cl2 (50 mL) under nitrogen. After 1.5 hours, triethylamine (5 mL, 36 mmol) and N-methylglycine methyl ester hydrochloride (2.1 g, 15 mmol) were added. The resulting mixture was stirred at room temperature overnight and then poured into water (200 mL) and CH2Cl2 (200 mL). The aqueous phase was washed with CH2Cl2 (100 mL) and the combined CH2Cl2 phases were washed successively with 1M H3PO4 (2 x 100 mL), water (100 mL), saturated NaHCO3 (50 mL), brine (100 mL) and dried over Na2SO4. Filtration and concentration left a pale brown foam which was filtered through a short column of silica gel with 1:1 ethyl acetate:hexane to obtain 2.53 g of the title compound as a pale yellow oil. NMR (200 MHz, CDCl3): δ2.87, 3.30 (2s, 3:1 ratio, 3H), 3.57-4.0 (m, 10H), 4.99 (d, 1H, J=17 Hz), 7.05-7.3 (m, 3H), 7.6-7.9 (m, 2H);

Fuente