With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.153-94-6,H-D-Trp-OH,as a common compound, the synthetic route is as follows.
General procedure: General procedure B A solution of amino nucleophile (3 equiv.), triethylamine (10 equiv.), and Intermediate 1 (1 equiv.) was stirred in dioxane and water (2:1 ratio) at 90 C until complete consumption of starting material was observed by LC/MS. The solution was diluted withiN hydrochloric acid and dichloromethane. The layers were then separated and thelayer was extracted with dichloromethane. The organics were combined, dried over magnesium sulfate, filtered, and the solvent was removed in vacuo. Purification yielded theproduct. The title compound was prepared following general procedure B, except D-tryptophan was the amine reactant and the contents were heated at 100 C for 18 h as a solution in THF/water (2:1). The contents were treated with 3N HC1 solution, solvent was removed in vacuo, and the resulting solid was washed with H20, then purified via reverse phase HPLC utilizing a 5-75 % acetonitrile/water gradient to deliver the desired compound, Compound 1-108 (3.5 mg, 16 %) as a clear oil.1H-NMR (500 MHz, CD3OD) oe 8.85 (d, 1 H), 8.16 (d, 1 H), 7.69 (d, 1 H), 7.33-7.27 (m, 1 H),7.17 (d, 1 H), 7.13-7.05 (m, 4 H), 7.01-6.96 (m, 1 H), 6.95-6.89 (m, 3 H), 5.97 (s, 2 H), 5.50 (dd, 1 H), 3.70 (dd, 1 H), 3.28 (d, 1 H).
As the paragraph descriping shows that 153-94-6 is playing an increasingly important role.
Reference£º
Patent; NAKAI, Takashi; MOORE, Joel; PERL, Nicholas Robert; IYENGAR, Rajesh R.; MERMERIAN, Ara; IM, G-Yoon Jamie; LEE, Thomas Wai-Ho; HUDSON, Colleen; RENNIE, Glen Robert; JIA, James; RENHOWE, Paul Allen; BARDEN, Timothy Claude; YU, Xiang Y; SHEPPECK, James Edward; IYER, Karthik; JUNG, Joon; WO2014/144100; (2014); A2;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI