1403576-45-3

Upstream product

• 67-56-1 methanol 
• 2033-24-1 cycl-isopropylidene malonate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 115655-70-4 (S) tert-butyl 2-(1H-imidazole-1-carbonyl)pyrrolidine-1-carboxylate 

Downstream Products

• 1403576-46-4 methyl (2'S)-3-(2'-pyrrolidinyl)-3-oxopropanoate trifluoroacetate salt 

Relevant academic research and scientific papers

L-Proline and related chiral heterocyclic amino acids as scaffolds for the synthesis of functionalized 2-amino-1,3-selenazole-5-carboxylates

[Figure not available: see fulltext.] A series of methyl 2-amino-1,3-selenazole-5-carboxylates possessing a chiral pyrrolidin-2-yl, piperidin-2-yl, or piperidin-3-yl substituent at the C-4 atom of the heteroaromatic ring was designed and synthesized. In the first stage of the synthesis, the carboxylic acid functional group of the L-proline or related chiral heterocyclic amino acid was converted to the corresponding β-keto ester, which was then α-brominated with N-bromosuccinimide. The subsequent reaction of the α-brominated β-keto ester with selenourea afforded the target methyl 2-amino-1,3-selenazole-5-carboxylate. The structures of the novel heterocyclic compounds were confirmed by 1H, 13C, and 77Se NMR spectroscopy and HRMS.

Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2- oxazole-4-carboxylates as new amino acid-like building blocks

A convenient and efficient synthesis of novel achiral and chiral heterocyclic amino acid-like building blocks was developed. Regioisomeric methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates were prepared by the reaction of β-enamino ketoesters (including azetidine, pyrrolidine or piperidine enamines) with hydroxylamine hydrochloride. Unambiguous structural assignments were based on chiral HPLC analysis, 1H, 13C, and 15N NMR spectroscopy, HRMS, and single-crystal X-ray diffraction data.

Bicyclic enol cyclocarbamates inhibit penicillin-binding proteins

Natural products form attractive leads for the development of chemical probes and drugs. The antibacterial lipopeptide Brabantamide A contains an unusual enol cyclocarbamate and we used this scaffold as inspiration for the synthesis of a panel of enol cyclocarbamate containing compounds. By equipping the scaffold with different groups, we identified structural features that are essential for antibacterial activity. Some of the derivatives block incorporation of hydroxycoumarin carboxylic acid-amino d-alanine into the newly synthesized peptidoglycan. Activity-based protein-profiling experiments revealed that the enol carbamates inhibit a specific subset of penicillin-binding proteins in B. subtilis and S. pneumoniae.

Asymmetric syntheses of functionalized pyrrolizidin-3-ones

The syntheses of 1- and 7-hydroxypyrrolizidin-3-ones are described via asymmetric catalytic hydrogenation or diastereoselective reduction of ketones as key steps. 2, 7-Disubstituted pyrrolizidin-3-ones are also prepared. The second chiral center is create