Реакция #1884986

Уравнение реакции

sodium hydride

N-t-Boc-L-homoserine

allyl bromide

→

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

Выход 93.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was warmed up to rt
2. 2
   workup.STIRRINGstirred for 2 h
3. 3
   КонцентрированиеIt was then concentrated in vacuo
4. 4
   workup.ADDITIONThe residue was diluted with water
5. 5
   Промывкаsequentially washed with hexane and ether
6. 6
   ЭкстракцияThis acidic aqueous solution was extracted with ethyl acetate
7. 7
   СушкаThe organic phase was dried (MgSO4)
8. 8
   Концентрированиеconcentrated in vacuo

Методика

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).

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