With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23190-16-1,(1R,2S)-2-Amino-1,2-diphenylethanol,as a common compound, the synthetic route is as follows.
125 mL of ethanol, 95 mL of water and 5.6 mL of 1 N hydrochloric acid were added to 2.4 g (5.60 mmol) of a mixture of the sodium salt of (3R)-3-benzyloxycarbonylamino-(S)-1-amino(sulfoamino)phosphinyl-2-piperidone and the sodium salt of (3R)-3-benzyloxycarbonylamino-(R)-1-amino(sulfoamino)phosphinyl-2-piperidone at about 1:1, and 2.63 mg (12.3 mmol) of (1R,2S)-(-)-2-amino-1,2-diphenylethanol; and the reaction liquid was stirred while being heated. Both compounds were completely dissolved at an inner temperature of about 50C, heating was stopped, and the reaction liquid was left till the inner temperature becomes room temperature. The precipitated crystal was taken through a filter, and 1.95 g of a salt of (3R)-3-benzyloxycarbonylamino-(S)-1-amino(sulfoamino) phosphinyl-2-piperidone with 2{(1R,2S)-(-)-2-amino-1,2-diphenylethanol} (2.34 mmol, an optical purity (d.e.) of 95.6%, and a yield of 42%) was obtained. As a result of measuring the optical purity (d.e.) of the filtrate, the filtrate proved to contain (3R)-3-benzyloxycarbonylamino-(R)-1-amino(sulfoamino)phosphinyl-2-piperidone of 83.4% (d.e.). salt of (3R)-3-benzyloxycarbonylamino-(S)-1-amino(sulfoamino)phosphinyl-2-piperidone with 2{(1R,2S)-(-)-2-amino-1,2-diphenylethanol}1H-NMR (200MHzFT, TMS, CD3OD) 1.55-1.77 (2H, m), 1.85-2.05 (2H, m), 3.00-3.80 (2H, m), 4.18-4.30 (3H, m), 4.86 (2H, d, J=4.8 Hz), 5.08 (2H, s), 7.07-7.43 (25H, m)
As the paragraph descriping shows that 23190-16-1 is playing an increasingly important role.
Reference£º
Patent; Nippon Kayaku Kabushiki Kaisha; ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI; EP1457494; (2004); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare