Reaktion #83067

Reaktionsgleichung

product

2,5-Anhydro-4-bromo-3,4-dideoxy-D-erythro-pentonic acid

1-hydroxybenzotriazole

1-benzyloxycarbonyl piperazine

dicyclohexylcarbodiimide

→

desired product

Ausbeute 57.4%

4-(2,5-Anhydro-4-bromo-3,4-dideoxy-D-erythro-pentonoyl)-1-piperazinecarboxylic acid phenylmethyl ester

Ausbeute 57.4%

Lösungsmittel

methylene chloride

dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe stirring continued overnight
2. 2
   Sonstigeat room temperature
3. 3
   Extraktionextracted with chloroform
4. 4
   SonstigeThe organic layer is dried
5. 5
   Einengenconcentrated in vacuo
6. 6
   Sonstigethe residue purified by chromatography (silica gel: 10-80% ethyl acetate/hexane)

Vorschrift

A mixture of 0.941 g of product from Example 150, 0.652 g of 1-hydroxybenzotriazole, 1.17 g of 1-benzyloxycarbonyl piperazine, 1.39 g of dicyclohexylcarbodiimide and 8 ml of dry methylene chloride is stirred at room temperature for 1 hour. Five ml of dimethylformamide is added and the stirring continued overnight at room temperature. The reaction mixture is diluted with water and extracted with chloroform. The organic layer is dried, concentrated in vacuo and the residue purified by chromatography (silica gel: 10-80% ethyl acetate/hexane) to give 1.1 g of the desired product.

Quelle