Reacción #219363

Ecuación de reacción

3-(2-Hydroxymethyl-4-tert-butoxycarbonylamino-5-methyl-phenyl)-2-(R)-benzyloxycarbonylamino-propionic acid methyl ester

Triethylamine

methanesulfonyl chloride

→

Title compound

Rendimiento 91.0%

3-(2-Chloromethyl-4-tert-butoxycarbonylamino-5-methyl-phenyl)-2-(R)-benzyloxycarbonylamino-propionic acid methyl ester

Rendimiento 91.0%

Disolventes

dichoromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadothen washed once with water, twice with 1N hydrochloric acid
2. 2
   SecadoOrganics were dried (magnesium sulfate)
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated in vacuo

Procedimiento

3-(2-Hydroxymethyl-4-tert-butoxycarbonylamino-5-methyl-phenyl)-2-(R)-benzyloxycarbonylamino-propionic acid methyl ester (510 mg, 1.1 mmol) was dissolved in dichoromethane (5 mL). Triethylamine (250 μL, 1.8 mmol) was added to the mixture followed by methanesulfonyl chloride (100 μL, 1.3 mmol). Mixture was stirred at room temperature for 1.5 hours. Mixture was diluted with dichloromethane then washed once with water, twice with 1N hydrochloric acid, and once with brine. Organics were dried (magnesium sulfate), filtered and concentrated in vacuo. Title compound was obtained as white solid in 91% yield. MS m/e (M+H)+=491.

Fuente