Reacción #1884986

Ecuación de reacción

sodium hydride

N-t-Boc-L-homoserine

allyl bromide

→

(S)-4-allyloxy-2-(tert-butoxycarbonylamino)butyric acid

Rendimiento 93.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was warmed up to rt
2. 2
   workup.STIRRINGstirred for 2 h
3. 3
   ConcentraciónIt was then concentrated in vacuo
4. 4
   workup.ADDITIONThe residue was diluted with water
5. 5
   Lavadosequentially washed with hexane and ether
6. 6
   ExtracciónThis acidic aqueous solution was extracted with ethyl acetate
7. 7
   SecadoThe organic phase was dried (MgSO4)
8. 8
   Concentraciónconcentrated in vacuo

Procedimiento

To a mixture of sodium hydride (913 mg, 22.8 mmoL) in DMF at 0° C. was added N-t-Boc-L-homoserine (2 g, 9.13 mmoL). This reaction mixture was stirred at 0° C. for 15 min, and then allyl bromide (1.38 g, 11.4 mmoL) was added. The mixture was warmed up to rt, and stirred for 2 h. It was then concentrated in vacuo. The residue was diluted with water, and sequentially washed with hexane and ether. The organic layers were discarded, and the aqueous layer was carefully adjusted to pH 3 with 1 N HCl. This acidic aqueous solution was extracted with ethyl acetate. The organic phase was dried (MgSO4), and concentrated in vacuo to yield 2.2 g (93%) of (S)-4-allyloxy-2-(tert-butoxycarbonylamino)butyric acid as a colorless oil. 1H NMR (300 MHz, CD3OD) δ 1.42 (s, 9 H), 1.80-1.90 (m, 1 H), 2.04-2.16 (m, 1 H), 3.50-3.54 (m, 2 H), 3.97 (d, J=4.39 Hz, 2 H), 4.23 (dd, J=8.78, 4.39 Hz, 1 H), 5.15 (d, J=10.25 Hz, 1 H), 5.26 (dd, J=17.38, 1.65 Hz, 1 H), 5.84-5.97 (m, 1 H).

Fuente