Reaktion #833088

Reaktionsgleichung

N-benzyloxycarbonyloxy-5-norbornen-2,3-dicarboximide

Sodium bicarbonate

5-hydroxylysine hydrochloride

→

III

Ausbeute 33.3%

N-Benzyloxycarbonyl-5-hydroxylysine

Ausbeute 33.3%

Lösungsmittel

acetonitrile

water

Acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigemost of the acetonitrile was removed in vacuo
2. 2
   workup.ADDITIONthe remaining solution was treated with hydrochloric acid
3. 3
   ExtraktionThe solution was extracted with ethyl acetate (50 ml)
4. 4
   Temperaturthe pH was increased to 5.5 with sodium hydroxide
5. 5
   Sonstigethe product was purified over Dowex 50W-2X
6. 6
   WaschenThe product was eluted with 3% pyridine in water
7. 7
   Einengenconcentrated to a small volume and freeze
8. 8
   Sonstigedried

Vorschrift

Sodium bicarbonate (4.2 g, 0.050 mol) and 5-hydroxylysine hydrochloride (2.50 g, 0.0126 mol) were dissolved in water (70 ml) with stirring at room temperature. Acetonitrile (40 ml) was added, followed by N-benzyloxycarbonyloxy-5-norbornen-2,3-dicarboximide (3.94 g, 0.0126 mol) in acetonitrile (30 ml) over 15 minutes. After 2 hours, most of the acetonitrile was removed in vacuo and the remaining solution was treated with hydrochloric acid to reduce the pH to 2.0. The solution was extracted with ethyl acetate (50 ml), the pH was increased to 5.5 with sodium hydroxide, and the product was purified over Dowex 50W-2X. The product was eluted with 3% pyridine in water, concentrated to a small volume and freeze dried to give III (1.24 g, 0.0042 mol, 33%); nmr (0.5 M NaOD in D2O)δ 1.4-2.1 (m, 4H, --CH2CH2 --), 3.1-3.5 (m, 2H, --NCH2CH ), 3.5-3.9 (m, 1H, --NCHRCO), 3.9-4.2 (m, 1H, --CH2CHOHCH2 --), 5.10 (s, 2H, --CH2O), 7.39 (s, 5H, --CH2O); mass spectrum (FAB): 297 (M+1).

Quelle