Reaktion #479197

Reaktionsgleichung

Fmoc-norvaline

thionyl chloride

→

title product

Ausbeute 109.1%

9-fluorenylmethoxycarbonyl-norvalinal

Ausbeute 109.1%

Lösungsmittel

ethylacetate

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe completion of the reaction (Rf=0.85)
2. 2
   EinengenThe reaction mixture was concentrated
3. 3
   WaschenThe organic layer was washed with three 200 ml portions of saturated sodium bicarbonate
4. 4
   SonstigeThe organic layer was dried
5. 5
   Einengenconcentrated

Vorschrift

To a chilled solution of Fmoc-norvaline (25 g, 73.75 mmol) in anhydrous methanol (469 mL) was added thionyl chloride (53.76 mL, 0.74 mol) over one hour. Thin layer chromatography in ethylacetate taken an hour later confirmed the completion of the reaction (Rf=0.85). The reaction mixture was concentrated and the remaining residue was picked-up in ethylacetate. The organic layer was washed with three 200 ml portions of saturated sodium bicarbonate followed by brine. The organic layer was dried and concentrated to afford the title product as a white solid (26.03 g) in quantitative yield. NMR δ ppm (CD3OD): 7.7 (m, 2H), 7.6 (m, 2H), 7.4 (m, 2H), 7.3 (m, 2H), 4.3 (m, 2H), 4.1 (m, 2H), 3.7 (s, 3H), 1.7 (m, 1H), 1.6 (m,1H), 1.4 (m, 2H), 0.95 (t, 3H).

Quelle