59524-07-1

The general procedure for the synthesis of benzyl 2-(((benzyloxy)carbonyl)amino)acrylate from benzyl ((benzyloxy)carbonyl)serine was as follows: first, 4-toluenesulfonyl chloride (TsCl) (2.0 eq.) and 4-dimethylaminopyridine (DMAP) (0.2 eq.) were added to an acetonitrile solution of N-Boc-DL-Ser-O-Me (1.0 eq.) ( 0.2 M, containing 4?molecular sieves (40 mg/mmol)) and the reaction was carried out at room temperature. Subsequently, 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) (5.0 eq.) was slowly added dropwise to the reaction mixture, and the color of the solution darkened during the dropwise addition. The reaction process was monitored by thin layer chromatography (TLC). After complete consumption of the raw materials, the reaction mixture was diluted with ethyl acetate and washed sequentially with saturated citric acid solution, water and brine. The organic phase was dried with anhydrous sodium sulfate and concentrated to obtain the crude product. Finally, the crude product was purified by fast column chromatography.

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[2] Synthetic Communications, 2016, vol. 46, # 11, p. 977 - 982
[3] Tetrahedron, 2007, vol. 63, # 42, p. 10534 - 10542