Reacción #1742187

Ecuación de reacción

3-nitrophenylacetic acid

sarcosine methyl ester hydrochloride

triethylamine

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

→

amide

Rendimiento 68.0%

N-Methyl-(3-nitrophenylacetyl)aminoacetic acid methyl ester

Rendimiento 68.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent removed in vacuo
2. 2
   workup.ADDITIONEthyl acetate (300 ml) was added to the residue
3. 3
   Otrothe mixture partitioned with 1M HCl (2×200 ml), saturated sodium bicarbonate solution (2×200 ml), water (200 ml) and brine (200 ml)
4. 4
   OtroThe organic phase was separated
5. 5
   Secadodried (MgSO4)
6. 6
   Otroevaporated in vacuo
7. 7
   OtroThe residue was chromatographed on silica gel

Procedimiento

To a stirred solution of 3-nitrophenylacetic acid (25 g, 0.14 mol), sarcosine methyl ester hydrochloride (20.2 g, 0.15 mol), triethylamine (20 ml, 0.15 mol) and 4-dimethylaminopyridine (17.7 g, 0.15 mol) in dichloromethane (300 ml) was added, under nitrogen, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (27.8 g, 0.15 mol). The mixture was stirred at room temperature for 18 h then the solvent removed in vacuo. Ethyl acetate (300 ml) was added to the residue and the mixture partitioned with 1M HCl (2×200 ml), saturated sodium bicarbonate solution (2×200 ml), water (200 ml) and brine (200 ml). The organic phase was separated, dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on silica gel, using petrol:ethyl acetate (1:1) as the eluant, to afford the title amide (25 g, 68%) as a yellow oil. 1H NMR (360MHz, CDCl3) δ3.13 (3H, s), 3.75 (3H, s), 3.88 (2H, s), 4.16 (2H, s), 7.26-7.65 (2H, m), 8.09-8.14 (2H, m). MS (CI, NH3), 284 (M+NH4+).

Fuente