860312-75-0

Upstream product

• 64-17-5 ethanol 
• 437713-03-6 methanesulfonic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenyl-propyl ester 
• 149451-80-9 (2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol 
• 220871-52-3 1(R,S)-<1'-(S)-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>oxirane 

Downstream Products

• 860312-76-1 (1S,2S)-2-[(tert-butoxycarbonyl)amino]-1-(ethoxymethyl)-3-phenylpropyl methanesulfonate 

Relevant academic research and scientific papers

Phenylamide and pyridylamide beta-secretase inhibitors for the treatment of alzheimer's disease

The present invention is directed to phenylamide and pyridylamide derivative compounds of which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.

Process research and development for an efficient synthesis of the HIV protease inhibitor BMS-232632

Development of an efficient and scalable process for the human immunodeficiency virus (HIV) protease inhibitor BMS-232632 1-[4-(pyridin-2-yl)phenyl]-5(S)-2,5-bis{[N-(methoxycarbonyl)L-tert- leucinyl]-amino}-4(S)-hydroxy-6-phenyl-2-azahexane, is described. The key step in the synthesis of the intermediate N-1-(tert-butyloxycarbonyl)-N-2-[4-(pyridin-2-yl)benzylidene]hydrazone (11) was the Pd-mediated coupling of boronic acid 9 with 2-bromopyridine. An efficient procedure was developed for the chemoselective reduction of hydrazone 11 to hydrazine carbamate 4. The key intermediate N-(tert-butyloxycarbonyl)-2(S)-amino-1-phenyl-3(R)-3,4-epoxy-butane (6) was prepared stereoselectively from chiral diol 10. The subsequent union of 4 and 6 followed by coupling with N-methoxycarbonyl-L-tert-leucine provided the free base BMS-232632 in high yield. Evaluation of a variety of salts and identification of bisulfate salt 19 with enhanced bioavallability are also described.