220035-13-2

Upstream product

• 108-24-7 acetic anhydride 
• 756462-76-7 (R)-1-benzyl-prop-2-enylamine 
• 4732-10-9 (RS)-3-Amino-4-phenyl-1-butene 
• 2018-61-3 (S)-2-acetylamino-3-phenylpropanoic acid 
• 63-91-2 L-phenylalanine 
• 133544-94-2 (S)-3-acetyl-4-benzyl-5-oxazolidinone 
• 220035-08-5 (S)-3-acetyl-5-dichloromethylene-4-benzyloxazolidine 

Downstream Products

• 103127-52-2 ((S)-1-benzylallyl)carbamic acid tert-butyl ester 
• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 

Relevant academic research and scientific papers

Preparation method for amprenavir intermediate

The invention relates to a synthesis method for an amprenavir intermediate, an anti-AIDS drug, in particular to a synthesis method for (2R,3S)-1,2-epoxy-3-(tert-butoxycarbonylamino)-4-phenylbutane. The synthesis method comprises the following steps: reacting L-phenylalanine, as a raw material, with acetic anhydride to generate N-acetyl-L-phenylalanine, and then carrying out a Mannich reaction, an Appel reaction and olefin epoxidation to obtain an intermediate. The method for preparing the (2R,3S)-1,2-epoxy-3-(tert-butoxycarbonylamino)-4-phenylbutane is reasonable in route, high in operability and high in yield, and facilitates industrial production.

Convenient method for synthesis of N-protected α-amino epoxides: Key intermediates for HIV protease inhibitors

A convenient method for synthesis of 2R,3S and 2S,3S N-Boc phenylalanine epoxides using readily available allylamine is described. Previous methods employed multistep synthetic routes from l-phenyl alanine that include use of m-chloroperbenzoic acid (m-CPBA) and a chromatographic method for purification of the desired diastereomers. Column purification could be eliminated by bringing in much improvement in the existing process. The process was further enhanced by replacing m-CPBA with oxone, an ecofriendly reagent advantageous for commercial application. The overall green process discussed involves the recovery and recycling of enantiomers of chiral allyl amines and judicial separation of diastereomers of the epoxides using simple economical methods.

A novel and facile synthesis of C2-symmetric HIV - Protease inhibitors

A facile synthesis of C2-symmetric HIV protease inhibitors 7 and 10 is described via a novel dichloromethylenation of oxazolidinone 1 and its conversion to allyl amine 3.

A New Approach for Chiral Allyl Amines via a Novel Dichloromethylenation of Oxazolidinones

A novel dichloromethylenation of oxazolidinones and their conversion to allyl amines 3a-e, key precursors for potential HIV protease inhibitors is described.