Reaktion #366990

Reaktionsgleichung

t-butoxycarbonyl threonine

O-benzylhydroxylamine HCl

N-hydroxybenzotriazole

dicyclohexylcarbodiimide

→

compound

Ausbeute 55.6%

N-Benzyloxy-t-butoxycarbonyl-threonine amide

Ausbeute 55.6%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   Sonstigeevaporated in vacuo
3. 3
   SonstigeThe residue was chromatographed on a 300 g silica gel column (
4. 4
   Waschenelution with chloroform and chloroform/ethyl acetate (3:1)

Vorschrift

A solution of 8.76 g of t-butoxycarbonyl threonine and the free amine from 6.4 g of O-benzylhydroxylamine HCl (ethyl acetate-sodium bicarbonate liberation) in 100 ml of tetrahydrofuran was treated with 6.12 g of N-hydroxybenzotriazole and 8.24 g of dicyclohexylcarbodiimide in 20 ml of tetrahydrofuran. The mixture was stirred under nitrogen for 26 hours, filtered, and evaporated in vacuo. The residue was chromatographed on a 300 g silica gel column (elution with chloroform and chloroform/ethyl acetate (3:1) yielding 7.2 g of compound. Crystallization from ether-hexane gave 4.18 g of the title compound.

Quelle