362480-01-1

Basic information

• Product Name: Carbamic acid, [(1S)-1-[(3,5-difluorophenyl)methyl]-2-(methoxymethylamino)-2-oxoethyl] -, 1,1-dimethylethyl ester
• CAS NO: 362480-01-1
• Molecular Formula: C16H22F2N2O4
• Molecular Weight: 344.358
• Mol File: 362480-01-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(1S)-1-[(3,5-difluorophenyl)methyl]-2-(methoxymethylamino)-2-oxoethyl] -, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S)-1-[(3,5-difluorophenyl)methyl]-2-(methoxymethylamino)-2-oxoethyl] -, 1,1-dimethylethyl ester(362480-01-1)
• EPA Substance Registry System: Carbamic acid, [(1S)-1-[(3,5-difluorophenyl)methyl]-2-(methoxymethylamino)-2-oxoethyl] -, 1,1-dimethylethyl ester(362480-01-1)

Safety Data

• Hazardous Substances Data: 362480-01-1(Hazardous Substances Data)

Upstream product

• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 205445-52-9 (2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propanoic acid 
• 1117-97-1 N,0-dimethylhydroxylamine 

Downstream Products

• 845543-57-9 tert-butyl [(1S)-1-(3,5-difluorobenzyl)-2-hydroxyethyl]carbamate 
• 860312-97-6 C₁₈H₂₇F₂NO₃ 
• 845543-61-5 (S)-N,N-dibenzyl-3,5-difluorophenyl-alaninal 
• 845543-66-0 (R)-tert-butyl 2-((1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl)pyrrolidine-1-carboxylate 
• 1221264-41-0 (S)-2-amino-3-(3,5-difluorophenyl)-N-methoxy-N-methylpropanamide 
• 1221264-42-1 (S)-2-(dibenzylamino)-3-(3,5-difluorophenyl)-N-methoxy-N-methylpropanamide 
• 1221264-43-2 (R)-tert-butyl 2-((1S,2S)-2-(dibenzylamino)-3-(3,5-difluorophenyl)-1-hydroxypropyl)pyrrolidine-1-carboxylate 
• 388071-27-0 tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate 
• 388071-41-8 (1S,2R)-[1-(3,5-difluorobenzyl)-2-hydroxy-3-(3-iodobenzylamino)propyl]-carbamic acid tert-butyl ester 
• 388063-46-5 N₁-{(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-iodobenzyl)amino]propyl}-5-methyl-N₃,N₃-dipropylisophthalamide 
• 388071-25-8 tert-butyl (1S)-3-bromo-1-(3,5-difluorobenzyl)-2-oxopropylcarbamate 
• 388071-26-9 tert-butyl (1S,2S)-3-bromo-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate 
• 1361944-83-3 C₁₅H₁₉F₂NO₃ 
• 531521-47-8 tert-butyl (1S)-1-(3,5-difluorobenzyl)-2-oxobut-3-enylcarbamate 

Relevant articles and documents

Design, synthesis, and biological evaluation of novel fluorinated ethanolamines

The preparation of novel fluorinated allylamines and their use as key fragments for the stereoselective synthesis of hydroxyethyl secondary amine (HEA)-type peptidomimetics is described. Our strategy employs chiral sulfinyl imines as synthesis intermediates, by treatment of hemiaminal precursors with two equivalents of vinylmagnesium bromide. The subsequent oxidation of the allylic amines to the corresponding epoxides was achieved by treatment with methyl(trifluoromethyl)dioxirane. Finally, epoxide ring opening with a range of nitrogen nucleophiles provided a library of HEA-derived peptidomimetics with a phenyldifluoromethylene moiety. The biological evaluation of these derivatives revealed compounds with remarkable BACE1 inhibitory activity. Docking studies revealed the influence of the fluorine atoms in the binding mode of the synthesized ligands. Furthermore, the biological evaluation of our final products and synthesis intermediates led to the discovery of compounds with antimicrobial activity against Mycobacterium and Nocardia species.

Discovery and SAR of isonicotinamide BACE-1 inhibitors that bind β-secretase in a N-terminal 10s-loop down conformation

A series of low-molecular weight 2,6-diamino-isonicotinamide BACE-1 inhibitors containing an amine transition-state isostere were synthesized and shown to be highly potent in both enzymatic and cell-based assays. These inhibitors contain a trans-S,S-methyl cyclopropane P3 which bind BACE-1 in a 10s-loop down conformation giving rise to highly potent compounds with favorable molecular weight and moderate to high susceptibility to P-glycoprotein (P-gp) efflux.