Reacción #92696

Ecuación de reacción

(3S)-3-amino-2-hydroxyhexanoic acid hydrochloride

hydrogen chloride dioxane

→

methyl (2R,3S)-3-amino-2-hydroxyhexanoate

methyl (2S,3S)-3-amino-2-hydroxyhexanoate

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent was evaporated under reduced pressure
2. 2
   workup.ADDITIONA saturated aqueous sodium hydrogen carbonate solution and chloroform were added
3. 3
   Otroa layer separation operation
4. 4
   LavadoThe organic layer was washed with saturated brine
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Otrothe solvent was evaporated under reduced pressure
7. 7
   OtroThe residue was purified by silica gel column chromatography

Procedimiento

To a solution of 1 g of (3S)-3-amino-2-hydroxyhexanoic acid hydrochloride in 10 mL of methanol was added 10 mL of a 4 M hydrogen chloride/dioxane solution, followed by stirring overnight, and the solvent was evaporated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution and chloroform were added thereto to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 425 mg of methyl (2R,3S)-3-amino-2-hydroxyhexanoate and 130 mg of methyl (2S,3S)-3-amino-2-hydroxyhexanoate.

Fuente