반응 #157288

반응 방정식

sodium ethoxide

sodium hydride

sodium ethoxide

methyliodide

methyliodide

N-Boc-L-serine

→

product

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

용매

THF

methanol

THF

반응 조건

후처리

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
   기타After 18 hours the reaction mixture is evaporated to dryness
4. 4
   세척The residue is washed with water and ether
5. 5
   추출extracted
6. 6
   추출extracted with ethyl acetate and dichloromethane

실험 절차

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.

출처