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ChemicalBook CAS DataBase List 7-Bromo-DL-tryptophan
852391-45-8

7-Bromo-DL-tryptophan synthesis

4synthesis methods
-

Yield:-

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane; for 6 h;Reflux;

Steps:



To a solution of rac-18 in dioxane (60 ml) was added HCl (6 M,60ml). The reaction mixture was heated to reflux for 6 h before the solvent was removed in vacuo. The crude residue was dissolved in NaOH (aqueous, 3 M, 50 ml). Then water (100 ml), THF (150 ml), Boc2O (9.2 g, 42.2 mmol) was added and the reaction mixture was stirred at rt overnight. The solvent was removed in vacuo and the resulting mixture was diluted with EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4, and concentratedto give rac-19 (9.90 g, 70%) was brown solid. The crude residue used directly for the next step without further purification.

References:

Zhao, Ji-Chen;Yu, Shun-Ming;Qiu, Hai-Bo;Yao, Zhu-Jun [Tetrahedron,2014,vol. 70,# 19,p. 3197 - 3210]

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