N-Acetyl-D-Glucosamine → D-Glucosamine
Reaction equation
C([NH:4][C@@H:5]1[C@@H:11]([OH:12])[C@H:10]([OH:13])[C@@H:9]([CH2:14][OH:15])[O:8][CH:6]1[OH:7])(=O)C.Cl.OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1N>O>[OH:7][CH:6]1[O:8][C@H:9]([CH2:14][OH:15])[C@@H:10]([OH:13])[C@H:11]([OH:12])[C@H:5]1[NH2:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The synthesis of N-acetyl-D-glucosamine from D-glucosamine hydrochloride was performed in a single synthetic step as previously described (Zhu, et al. J Org Chem 71, 466-479, the method of which is herein incorporated by reference). Briefly, to a solution of the D-glucosamine hydrochloride salt (150 mg, 0.6 mmol) in water was added Dowex 200-400 mesh (OH—) anion-exchange resin and the pH was adjusted to 7.5. The resin was removed by filtration, yielding a D-glucosamine solution in 6 mL of water. To this solution was added 13C2-sodium acetate (1.1 eq, Cambridge Isotope Laboratories) as a pre-dissolved solution in water and 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (1.1 eq) as a pre-dissolved solution in 10 mL ethanol. The total reaction volume was brought to 40 mL by addition of ethanol. The reaction was covered in foil and stirred for 36 h at RT. This reaction was repeated using 1-13C,15N-D glucosamine hydrochloride (Isotech) as the starting material. After ethanol evaporation under reduced pressure, the crude products were purified by silica gel chromatography using a 10:4:3 mixture of ethyl acetate:pyridine:water, dried, filtered, lyophilized and stored at −20° C.
Workup
- customThe resin was removed by filtration
Sources & evidence
- ORD record
- ord-aa550a5b5abc411b8ae9402093ee2cf7
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09410966B2
Reaction notes
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