Reaktion #46098

Reaktionsgleichung

sodium hydride

N-t-Boc-L-homoserine

allyl bromide

→

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

Ausbeute 93.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was warmed up to rt
2. 2
   workup.STIRRINGstirred for 2 h
3. 3
   EinengenIt was then concentrated in vacuo
4. 4
   workup.ADDITIONThe residue was diluted with water
5. 5
   Waschensequentially washed with hexane and ether
6. 6
   ExtraktionThis acidic aqueous solution was extracted with ethyl acetate
7. 7
   TrocknenThe organic phase was dried (MgSO4)
8. 8
   Einengenconcentrated in vacuo

Vorschrift

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, 9H), 1.80-1.90 (m, 1H), 2.04-2.16 (m, 1H), 3.50-3.54 (m, 2H), 3.97 (d, J=4.39 Hz, 2H), 4.23 (dd, J=8.78, 4.39 Hz, 1H), 5.15 (d, J=10.25 Hz, 1H), 5.26 (dd, J=17.38, 1.65 Hz, 1H), 5.84-5.97 (m, 1H).

Quelle