Reacción #1599897

Ecuación de reacción

4-Nitro-benzoyl chloride

methylamino-acetic acid methyl ester hydrochloride

triethyl-amine

→

[Methyl-(4-nitro-benzoyl)-amino]-acetic acid methyl ester

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoAfter 2 days the rxn was washed with water (1×10 mL), 1 M HCl (2×10 mL), water (1×10 mL) and satd NaHCO3 (2×10 mL)
2. 2
   SecadoAfter drying over MgSO4, filtration through silica with a 10:1 DCM
3. 3
   Lavadoi-PrOH wash
4. 4
   Otroconcd, the product was purified by MPLC (silica; 0-->10% i-PrOH in DCM gradient)
5. 5
   Otroyielding a pale yellow-orange solid (1.394 g; 73%) as
6. 6
   workup.ADDITIONa mix of rotamers

Procedimiento

4-Nitro-benzoyl chloride (1.396 g; 7.52 mmol), methylamino-acetic acid methyl ester hydrochloride (1.264 g; 9.06 mmol) and triethyl-amine (2.40 mL; 17.2 mmol) were reacted in DCM (35 mL). After 2 days the rxn was washed with water (1×10 mL), 1 M HCl (2×10 mL), water (1×10 mL) and satd NaHCO3 (2×10 mL). After drying over MgSO4, filtration through silica with a 10:1 DCM:i-PrOH wash and concd, the product was purified by MPLC (silica; 0-->10% i-PrOH in DCM gradient) yielding a pale yellow-orange solid (1.394 g; 73%) as a mix of rotamers. 1H NMR (CDCl3; major rotamer) δ 8.31 (m, 2H), 7.66 (m, 2H), 4.31 (s, 2H), 3.82 (s, 3H), 3.03 (s, 3H).

Fuente