Reaktion #48239

Reaktionsgleichung

2-hydroxyhexadecanoic acid

(E,4S)-1-(benzyloxy)-1-oxooct-2-en-4-aminium chloride

HOBt

→

Benzyl(E,4S)-4-[(2-hydroxydodecanoyl)amino]oct-2-enoate

Lösungsmittel

CH2Cl2

Et3N

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe organic layer was washed with brine
2. 2
   Trocknendried over Na2SO4
3. 3
   Sonstigeevaporated under reduced pressure
4. 4
   SonstigeThe residue was purified by column chromatography (CHCl3/MeOH 98/2)

Vorschrift

To a stirred solution of 2-hydroxyhexadecanoic acid (0.54 g, 2.0 mmol) and (E,4S)-1-(benzyloxy)-1-oxooct-2-en-4-aminium chloride (0.28 g, 1.0 mmol) in CH2Cl2 (5 mL), Et3N (0.3 mL) and subsequently WSCI (0.57 g, 3.0 mmol) and HOBt (0.32 g, 2.0 mmol) were added at 0° C. The reaction mixture was stirred for 1 h at 0° C. and at room temperature for 1 day. The organic layer was washed with brine, dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography (CHCl3/MeOH 98/2). Yield 0.33 g (75%); [α]D−10.3 (c 0.5 CHCl3);

Quelle