Reacción #58625

Ecuación de reacción

3-(4-chlorophenyl)-2-phenylpropionic acid

3-(4-Chlorophenyl)-2-phenylpropanoic acid

oxalyl chloride

N-methoxy-N-methylamine hydrochloride

triethyl amine

→

crude product

N-Methoxy-N-methyl-3-(4-chlorophenyl)-2-phenylpropanamide

Disolventes

ether

methylene chloride

dimethylformamide

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated to dryness
2. 2
   Otroto give the crude acyl chloride, which
3. 3
   Otrowas used without further purification
4. 4
   Lavadosuccessively washed with water, dilute aqueous sodium hydrogen sulfate and brine
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated to dryness

Procedimiento

To a solution of 3-(4-chlorophenyl)-2-phenylpropionic acid (Step B, 14 g, 55 mmol) in methylene chloride (125 mL) at 0° C. were added dropwise dimethylformamide (50 μL) and oxalyl chloride (14 g, 0.11 mol). The reaction was allowed to warm to room temperature overnight and concentrated to dryness to give the crude acyl chloride, which was used without further purification. To a solution of the crude acyl chloride in methylene chloride (250 mL) was added N-methoxy-N-methylamine hydrochloride (11 g, 0.11 mol) and triethyl amine (dried over activated molecular sieves, 30 mL, 0.22 mol) at 0° C. After stirring at room temperature for 4 h, the reaction mixture was diluted with ether (500 mL) and successively washed with water, dilute aqueous sodium hydrogen sulfate and brine, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness to give the crude product, which was used without further purification. 1H NMR (500 MHz, CD3OD): δ 7.4-7.1 (m, 9H), 4.38 (br, 1H), 3.48 (s, 3H), 3.35 (dd, 1H), 3.10 (s, 3H), 2.92 (dd, 1H); LC-MS: m/e 304 (3.6 min).

Fuente