Gluconic Acid → Gluconic acid hydrazide
Reaction equation
[O:1]=[C:2](O)[C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].C([NH:21][NH2:22])(OC(C)(C)C)=O>CO>[O:1]=[C:2]([NH:21][NH2:22])[C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Five grams of gluconic acid were suspended in 15 ml of warm MeOH. After the complete dissolution 4 grams of monoBOC-hydrazine were added to the reaction vessel. The solution was refluxed for 36 h. After the addition of monoBOC-hydrazine the suspension disappeared. At the end, the reaction showed a white precipitate which contained most of the product. The solvent was removed under vacuum and the solid product was extracted in a mixture of NaOH sol. 0.1 N/chloroform. The organic phase was removed while the aqueous phase was passed through anionic exchanger resin and lyophilized. Finally, product was dissolved in cold MeOH and deprotected from the BOC-function by bubbling HCl gas into the solution over 30′. The purity of the protected and the deprotected product was checked by TLC, HPLC and the identity was confirmed by ESI-MS.