23632-68-0

Upstream product

• 507-19-7 t-butyl bromide 
• 23632-67-9 (S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid 
• 18595-34-1 tert-butyl fluoroformate 
• 75-65-0 tert-butyl alcohol 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 

Downstream Products

• 911033-98-2 (4S,5S)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-(trimethylsilyloxy)oxazolidine-3-carboxylate 
• 911034-11-2 (S)-4-[N-(benzyloxycarbonyl)-L-alanyl-L-valyl-L-leucyl]amino-6,6,6-trifluoro-5-oxohexanoic acid 
• 911034-09-8 (S)-4-[N-(benzyloxycarbonyl)-L-phenylalanyl-L-alanyl]amino-6,6,6-trifluoro-5-oxohexanoic acid 
• 911034-15-6 (S)-4-((S)-2-Benzyloxycarbonylamino-propionylamino)-6,6,6-trifluoro-5-hydroxy-hexanoic acid tert-butyl ester 
• 911034-17-8 (S)-tert-butyl 4-[N-(benzyloxycarbonyl)-L-alanyl]amino-6,6,6-trifluoro-5-oxohexanoate 
• 911034-00-9 (4S,5R)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-hydroxyoxazolidine-3-carboxylate 
• 911034-02-1 (4S)-tert-butyl 4-(benzyloxycarbonyl)amino-6,6,6-trifluoro-5-hydroxyhexanoate 
• 365217-97-6 5-tert-butyl 1-prop-2-en-1-yl 2-{[(benzyloxy)carbonyl]amino}-pentanedioate 
• 3967-19-9 (S)-2-benzyloxycarbonylaminopentanedioic acid 5-tert-butyl ester 1-ethyl ester 
• 56877-41-9 methyl 2(S)-2-benzyloxycarbonylamino-4-tert-butoxycarbonylbutanoate 
• 3886-08-6 5-tert-butyl N-benzyloxycarbonyl-L-glutamate 

Relevant academic research and scientific papers

Synthesis of glutamic acid and glutamine peptides possessing a trifluoromethyl ketone group as SARS-CoV 3CL protease inhibitors

Trifluoromethyl-β-amino alcohol 11 [(4S)-tert-butyl 4-amino-6,6,6-trifluoro-5-hydroxyhexanoate] was synthesized in five steps starting from Cbz-l-Glu-OH 5 where the key step involved the introduction of the trifluoromethyl (CF3) group to oxazolidinone 7, resulting in the formation of silyl ether 8 [(4S,5S)-benzyl 4-(2-(tert-butoxycarbonyl)ethyl)-5-(trifluoromethyl)-5-(trimethylsilyloxy)oxazolidine-3-carboxylate]. Compound 11 was then converted into four tri- and tetra-glutamic acid and glutamine peptides (1-4) possessing a CF3-ketone group that exhibited inhibitory activity against severe acute respiratory syndrome coronavirus protease (SARS-CoV 3CLpro).

Facile synthesis of tert-butyl ester of N-protected amino acids with tert-butyl bromide

A facile synthesis of a wide variety of N-benzyloxycarbonyl-amino acid-tert-butyl ester derivatives under mild conditions is described. N-protected amino acids were esterified with tert-butyl bromide in dimethylacetamide as solvent, in the presence of benzyltriethylammonium chloride (BTEAC)and a large excess of potassium carbonate. Many amino Z-acid-Tert-butyl esters that might be difficult to prepare by other methods have been synthesized in high yields by this procedure. The reaction is simple, unexpansive, easily scaled up, and proceeds without observable racemization.

TERT-BUTYL ESTERS OF N-PROTECTED AMINO ACIDS WITH TERT-BUTYL FLUOROCARBONATE (Boc-F)

Tert-butyl fluorocarbonate (Boc-F) is efficiently used for the synthesis of tert-butyl esters of N-protected amino acids.The reaction proceeds at room temperature and under mild conditions in the presence of triethylamine and 4-dimethylamino-pyridine.