Reacción #157288

Ecuación de reacción

sodium ethoxide

sodium hydride

sodium ethoxide

methyliodide

methyliodide

N-Boc-L-serine

→

product

(S)-2-tert-butoxycarbonylamino-3-methoxy-propionic acid

Disolventes

THF

methanol

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONUnder nitrogen a mixture of 74 ml abs
2. 2
   workup.STIRRINGThe suspension is stirred for 1 hour at ambient temperature
3. 3
   OtroAfter 18 hours the reaction mixture is evaporated to dryness
4. 4
   LavadoThe residue is washed with water and ether
5. 5
   Extracciónextracted
6. 6
   Extracciónextracted with ethyl acetate and dichloromethane

Procedimiento

Under nitrogen a mixture of 74 ml abs. THF and 6 ml abs. methanol is cooled to −70° C. and 2 g sodium hydride (55-65% dispersion) are added. The suspension is stirred for 0.4 hour at ambient temperature. Under nitrogen, 2.05 g N-Boc-L-serine are suspended in 100 ml abs. THF and 40 ml of the prepared sodium ethoxide solution are added. The suspension is stirred for 1 hour at ambient temperature and 1 ml methyliodide are added. After 1 hour the remainder of the sodium ethoxide solution and another 2 ml of methyliodide are added. After 18 hours the reaction mixture is evaporated to dryness. The residue is washed with water and ether and extracted. The water phase is acidified and extracted with ethyl acetate and dichloromethane. 0.52 g of the product are obtained.

Fuente