Yield:1101-67-3 64.8%

Reaction Conditions:

Stage #1: L-glutaminewith sodium hydrogencarbonate in acetone at 0; for 0.166667 h;
Stage #2: 5-(dimethylamino)naphth-1-ylsulfonyl chloride in acetone at 0 - 20; for 3.5 h;

Steps:

Synthesis and characterization of 1

0.12g Glutamine (0.821mmol) in flasks was dissolved in sodium bicarbonate solution (15.0ml, 0.10M). The mixed solution was cooled at 0°C ice-water bath for 10min. Then the solution of dansyl chloride (0.225g, 0.835mmol) in 15.0mL acetone was added dropwise to the above stirred glutamine solution. The reaction was stirred at 0°C ice-water bath for 30min, and then under room temperature for 3h [17,18]. After the completion of reaction, the acetone in the mixture was evaporated under reduced pressure. Then, the residue liquid was washed with Et₂O for three times (3×20.0mL). The aqueous layer was added HCl to pH 4.5, and was shook with ethyl acetate. The organic layer was separated and distilled under reduced pressure to give a crude residue. The product was further purified by column chromatography; finally the tawny solid product of 1 was obtained with a 64.8% yield. ESI-MS (m/z): 378.73; calcd for C₁₇H₂₁N₃O₅S, 379.43.

References:

Zhao, Meili;Ma, Liguo;Zhang, Min;Cao, Weiguang;Yang, Liting;Ma, Li-Jun [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2013,vol. 116,p. 460 - 465]