23632-68-0

Basic information

• Product Name: 4(S)-(2-tert-butoxycarbonylethyl)-5-oxo-oxazolidine 3-carboxylic acid benzyl ester
• Synonyms: 4(S)-(2-tert-butoxycarbonylethyl)-5-oxo-oxazolidine 3-carboxylic acid benzyl ester
• CAS NO: 23632-68-0
• Molecular Weight: 349.384
• Mol File: 23632-68-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4(S)-(2-tert-butoxycarbonylethyl)-5-oxo-oxazolidine 3-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4(S)-(2-tert-butoxycarbonylethyl)-5-oxo-oxazolidine 3-carboxylic acid benzyl ester(23632-68-0)
• EPA Substance Registry System: 4(S)-(2-tert-butoxycarbonylethyl)-5-oxo-oxazolidine 3-carboxylic acid benzyl ester(23632-68-0)

Safety Data

• Hazardous Substances Data: 23632-68-0(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 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 
• 911033-98-2 (4S,5S)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-(trimethylsilyloxy)oxazolidine-3-carboxylate 
• 56877-41-9 methyl 2(S)-2-benzyloxycarbonylamino-4-tert-butoxycarbonylbutanoate 
• 3886-08-6 5-tert-butyl N-benzyloxycarbonyl-L-glutamate 
• 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 

Relevant articles and documents

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).

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.