Reaction #1884986

Reaction equation

sodium hydride

N-t-Boc-L-homoserine

allyl bromide

→

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

Yield 93.0%

Solvents

DMF

Conditions

Workup

1. 1
   TemperatureThe mixture was warmed up to rt
2. 2
   workup.STIRRINGstirred for 2 h
3. 3
   ConcentrationIt was then concentrated in vacuo
4. 4
   workup.ADDITIONThe residue was diluted with water
5. 5
   Washsequentially washed with hexane and ether
6. 6
   ExtractionThis acidic aqueous solution was extracted with ethyl acetate
7. 7
   DryingThe organic phase was dried (MgSO4)
8. 8
   Concentrationconcentrated in vacuo

Procedure

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).

Source