反应 #1884986

反应方程式

sodium hydride

N-t-Boc-L-homoserine

allyl bromide

→

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

收率 93.0%

溶剂

DMF

反应条件

后处理

1. 1
   温度The mixture was warmed up to rt
2. 2
   workup.STIRRINGstirred for 2 h
3. 3
   浓缩It was then concentrated in vacuo
4. 4
   workup.ADDITIONThe residue was diluted with water
5. 5
   洗涤sequentially washed with hexane and ether
6. 6
   萃取This acidic aqueous solution was extracted with ethyl acetate
7. 7
   干燥The organic phase was dried (MgSO4)
8. 8
   浓缩concentrated in vacuo

实验过程

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).

来源