As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 114525-81-4, name is (R)-4-(tert-Butoxycarbonyl)thiomorpholine-3-carboxylic acid. This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 114525-81-4
Trifluoroacetic acid (4 mL, 23.5 mmol) was added to a stirred solution of (R)-4-(tert- butoxycarbonyl)thiomorpholine-3-carboxylic acid (1.0 g, 4.05 mmol) in CH2CI2 (20 mL), and the reaction mixture was stirred at room temperature for 2 h. Volatile byproducts were removed at reduced pressure and the residue was concentrated from toluene (2 x 20 mL) and dried under high vacuum for 30 min. The crude residue was dissolved in 1,4-dioxane (10 mL) and water (10 mL) was added followed by NaHCC (1.02 g, 12.15 mmol) and a solution of FMOC-C1 (1.04 g, 4.05 mmol) in 1,4-dioxane (10 mL). The reaction mixture was stirred at room temperature for 16 h. The mixture was concentrated under reduced pressure to remove volatile organic solvent and the residue was washed with MTBE (2 x 20 mL). The aqueous layer was acidified with IN aqueous HC1 to pH 2 and extracted with EtOAc (3 x 50 mL). The combined organic extracts were washed with brine solution (50 mL), dried over anhydrous a2S04, filtered and concentrated. The residue was purified by reverse phase column chromatography (CI 8; eluent: 10-100% acetonitrile/water) to afford the title compound (1.00 g) as a white semi-solid.
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Reference£º
Patent; MERCK SHARP & DOHME CORP.; BLIZZARD, Timothy Allen; BIFTU, Tesfaye; WO2013/148478; (2013); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem