Reacción #696729

Ecuación de reacción

3-(S)-amino-2-(R,S)-hydroxy-4-methylpentanoic acid

benzyl chloroformate

→

3-(S)-[(benzyloxycarbonyl)amino]-2-(R,S)-hydroxy-4-methylpentanoic acid

Rendimiento 92.0%

Disolventes

NaOH

dioxane

NaOH

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with ether
2. 2
   Extracciónextracted with ether (2×)
3. 3
   SecadoThe combined organic layers were dried over magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated in vacuo

Procedimiento

To a solution under an atmosphere of nitrogen containing 1.0 g (6.8 mmol) of 3-(S)-amino-2-(R,S)-hydroxy-4-methylpentanoic acid in 9.5 mL of 1 N NaOH and 10 mL of dioxane was added 1.43 g (8.4 mmol) of benzyl chloroformate. The pH was maintained above pH 8 with 1 N NaOH as needed. The reaction mixture was allowed to stir at room temperature overnight. The reaction was diluted with water and washed with ether. The aqueous layer was acidified with 1 N HCl to pH=2 and extracted with ether (2×). The combined organic layers were dried over magnesium sulfate, filtered and evaporated in vacuo to afford 1.75 g (92%) of 3-(S)-[(benzyloxycarbonyl)amino]-2-(R,S)-hydroxy-4-methylpentanoic acid as a light yellow viscous oil. FAB MS [M+H] m/z; Calcd: 282, Found: 282.

Fuente