반응 #978103

반응 방정식

4-iodobenzylbromide

glucosamine hydrochloride

diisopropylethylamine

→

4-iodobenzyl glucosamine

수율 9.4%

용매

DMF

DMF

반응 조건

후처리

1. 1
   기타the precipitated solid was removed from the supernatant
2. 2
   기타by decanting
3. 3
   기타Volatiles were removed from the supernatant
4. 4
   기타the resulting residue was separated on a si-gel column

실험 절차

Thus, a slurry of glucosamine hydrochloride (0.7 g) and diisopropylethylamine (0.6 mL) in DMF (2.0 mL) was stirred at 80° C. for 30 minutes. A solution of 4-iodobenzylbromide (0.4 g) in DMF (2 mL) was added to the reaction mixture, and the resulting mixture stirred for 18 hours. After the reaction mixture was cooled to room temperature, the precipitated solid was removed from the supernatant by decanting. Volatiles were removed from the supernatant, and the resulting residue was separated on a si-gel column using 10% aqueous MeCN as the eluent to yield 50 mg of pure 4-iodobenzyl glucosamine (compound TP012 in the scheme above). The purity of 4-iodobenzyl bromide, which can vary greatly from batch to batch if obtained from commercial suppliers, will affect the yields of this reaction accordingly. The compound 4-Iodobenzyl galactosamine can be prepared using a similar reaction scheme, starting from galactosamine hydrochloride and iodobenzyl bromide.

출처