176972-61-5

Upstream product

• 339190-43-1 N-benzylidene (S)-phenylalanine methyl ester 
• 110-54-3 hexane 
• 34351-19-4 (3S)-3-amino-1-chloro-4-phenyl-2-butanone hydrochloride 
• 79-22-1 methyl chloroformate 
• 67-63-0 isopropyl alcohol 
• 74-97-5 chlorobromomethane 
• 21369-64-2 n-hexyllithium 
• 41844-71-7 methyl (S)-2-methoxycarbonylamino-3-phenyl-propionate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 63-91-2 L-phenylalanine 
• 286019-77-0 (3S)-1-chloro-3-(diphenylmethylene)amino-4-phenyl-2-butanone 
• 120238-42-8 methyl (S)-2-(diphenylmethylideneamino)-3-phenylpropanoate 

Downstream Products

• 176972-62-6 [1(S)-benzyl-2(S)-hydroxy-chloropropyl]carbamic acid methyl ester 
• 177186-74-2 [1(S)-benzyl-2(R)-hydroxy-3-chloropropyl]carbamic acid methyl ester 
• 178680-13-2 [(1S,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propyl]-carbamic acid methyl ester 
• 136522-18-4 2-<3(S)-<amino>-2(R)-hydroxy-4-phenylbutyl>-N-tert-butyldecahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 137431-06-2 2-[3(S)-[(L-asparaginyl)-amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert-butyl-decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 136522-17-3 cis-N-butyldecahydro-2-<2(R)-hydroxy-4-phenyl-3(S)-aminobutyl>-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 127779-20-8 Saquinavir 

Relevant academic research and scientific papers

Process for producing alpha-aminoketones

An amino group of an α-amino acid ester is protected as an imine, and it is then reacted with a halomethyllithium to obtain an N-protected-α-aminohalomethylketone. Further, this N-protected-α-aminohalomethylketone is treated with an acid to obtain an α-aminohalomethylketone. This process is suited for industrial production, and can produce an α-aminohalomethylketone and its related compounds economically and efficiently.

Process for producing alpha-aminoketones

A process for producing α-aminohalomethyl ketones or N-protected α-aminohalomethyl ketones from specified 3-oxazolidin-5-one derivatives via 5-halomethyl-5-hydroxy-3-oxazolidine derivatives. By this process, α-aminohalomethyl ketones and compounds relating to them can be obtained efficiently and economically in industrial scale.

Practical synthesis of α-aminoalkyl-α′-chloromethylketone derivatives. Part 2: Chloromethylation of N-imine-protected amino acid esters

Chloromethylation of N-imine-protected amino acid esters followed by acid hydrolysis gave α-aminoalkyl-α′-chloromethylketone as a HCl salt form in good yield without racemization. The amino group was conveniently protected with carbamate protecting reagents to give various useful intermediates for the protease inhibitors.

Synthesis of the HIV-proteinase inhibitor Saquinavir: A challenge for process research

The task of process research, namely developing efficient, economically and technically as well as ecologically feasible syntheses in time, is demonstrated on the HIV-proteinase inhibitor Saquinavir (1), a complex molecule comprising six stereo-centres. Based on the first 26-step research synthesis furnishing a 10% overall yield, process research established a new, short 11-step synthesis affording a 50% overall yield.

Method of producing halogenated and alpha-aminoalchohols

A process for the manufacture of N-protected α-aminoketones and N-protected α-aminoalcohols of the formula STR1 wherein X is halogen, one of Q1 and Q2 is hydrogen and the other is hydroxy or Q1 and Q2 together are oxo, R1 is an amino protecting group and R2 is hydrogen or the characterizing group of an α-aminocarboxylic acid, starting from the corresponding lower alkyl N-protected α-aminocarboxylates via corresponding lower alkyl N-silyl protected α-aminocarboxylates.