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

Z Xu, J Singh, MD Schwinden, B Zheng…

Index: Xu, Zhongmin; Singh, Janak; Schwinden, Mark D.; Zheng, Bin; Kissick, Thomas P.; Patel, Bharat; Humora, Michael J.; Quiroz, Fernando; Dong, Lin; Hsieh, Dau-Ming; Heikes, James E.; Pudipeddi, Madhusudhan; Lindrud, Mark D.; Srivastava, Sushil K.; Kronenthal, David R.; Mueller, Richard H. Organic Process Research and Development, 2002 , vol. 6, # 3 p. 323 - 328

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Citation Number: 61

Abstract

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- ...