Reacción #1453606

Ecuación de reacción

N-{[(phenylmethyl)oxy]carbonyl}-D-alanine

EDC

sarcosine methyl ester hydrochloride

1-hydroxybenzotriazole

4-methylmorpholine

→

methyl N-{[(phenylmethyl)oxy]carbonyl}-D-alanyl-N-methylglycinate

Rendimiento 88.0%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred overnight
2. 2
   Lavadowas then washed with water (500 mL), 1 N aqueous HCl (2×300 mL), and brine (300 mL)
3. 3
   SecadoThe organic phase was dried over anhydrous Na2SO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo

Procedimiento

To a mixture of N-{[(phenylmethyl)oxy]carbonyl}-D-alanine (133.53 g, 598.2 mmol) in DCM (1100 mL) was added powdered sarcosine methyl ester hydrochloride (83.49 g, 598.2 mmol), 1-hydroxybenzotriazole (80.81 g, 598.1 mmol), and 4-methylmorpholine (242 mL, 2201 mmol). The mixture was stirred for 10 min, and then EDC (114.68 g, 598.2 mmol) was added. The mixture was stirred overnight, and was then washed with water (500 mL), 1 N aqueous HCl (2×300 mL), and brine (300 mL). The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give crude methyl N-{[(phenylmethyl)oxy]carbonyl}-D-alanyl-N-methylglycinate (162.35 g, 88% yield) as a yellow oil. LCMS: (M+H)+: 309.0.

Fuente