107020-12-2

Usage

Uses

Used in Organic Synthesis:
(S)-N-BOC-AZETIDINE-2-CARBOXYLIC ACID METHYL ESTER is used as a versatile intermediate for the preparation of various pharmaceutical compounds and natural products. Its BOC-protected structure and methyl ester functionality contribute to its utility in creating complex molecules with enhanced stability and reactivity.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-N-BOC-AZETIDINE-2-CARBOXYLIC ACID METHYL ESTER is used as a key building block for the synthesis of bioactive molecules. Its unique structure allows for the development of new drugs with potential therapeutic applications, taking advantage of its stability and reactivity to create novel pharmaceutical agents.
Used in Natural Product Synthesis:
(S)-N-BOC-AZETIDINE-2-CARBOXYLIC ACID METHYL ESTER is also utilized in the synthesis of natural products, where its BOC protection and methyl ester group facilitate the construction of complex natural compounds with potential biological activities. This makes it a valuable tool in the discovery and development of new natural product-based therapeutics.

InChI:InChI=1/C10H17NO4/c1-10(2,3)15-9(13)11-6-5-7(11)8(12)14-4/h7H,5-6H2,1-4H3

Upstream product

• 51077-14-6 (S)-1-(t-butoxycarbonyl)azetidine-2-carboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 67-56-1 methanol 
• 74-88-4 methyl iodide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 186581-53-3 diazomethane 
• 69684-70-4 methyl (2S)-azetidine-2-carboxylate 

Downstream Products

• 161511-85-9 2-(S)-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester 
• 100188-44-1 methyl (S)-(-)-2-oxoazetidine-4-carboxylate 
• 98045-03-5 α-methyl N-(tert-butoxycarbonyl)aspartate 
• 105443-94-5 (S)-2-carbamoyl-azetidine-1-carboxylic acid tert-butyl ester 
• 910824-86-1 (S)-1-(N-tert-butyloxycarbonylazetidin-2-yl)-3-cyclohexylamino-3-(thiazol-2-yl)prop-2-en-1-one 
• 144062-00-0 N-benzyloxycarbonyl azetidine-2-carboxylate methyl ester 
• 69684-70-4 methyl (2S)-azetidine-2-carboxylate 

Relevant academic research and scientific papers

Mechanistic interrogation of the asymmetric lithiation-trapping of N-thiopivaloyl azetidine and pyrrolidine

A fundamental mechanistic study of the s-BuLi/chiral diamine-mediated lithiation-trapping of N-thiopivaloyl azetidine and pyrrolidine is reported. We show that lithiated thiopivalamides are configurationally unstable at -78 °C. Reaction then proceeds via a dynamic resolution of diastereomeric lithiated intermediates and this accounts for the variable sense and degree of asymmetric induction observed compared to N-Boc heterocycles.

AMINOAZINE AMIDES

The disclosure provides novel compounds having the general formula (I) or a pharmaceutically acceptable salt, solvate or salt of the solvate thereof, compositions including the compounds and methods of using the compounds.

Synthesis and Homologation of an Azetidin-2-yl Boronic Ester with α-Lithioalkyl Triisopropylbenzoates

An α-boryl azetidine, obtained by α-lithiation-borylation of N-Botc azetidine, undergoes reaction with α-triisopropylbenzoyloxy organolithiums to give homologated boronic esters that can be further oxidized, homologated, arylated, and deprotected to give

Selective cleavage of carbamate protecting groups from aziridines with otera's catalyst

Otera's distannoxane catalyst was found to promote the cleavage of carbamate groups from N-protected aziridines. This method enables the chemoselective cleavage of an aziridinyl N-carbobenzyloxy (Cbz) group in the presence of other N-Cbz groups. The selec

AZETIDINE COMPOUNDS AS OREXIN RECEPTOR ANTAGONISTS

The invention relates to novel azetidine compounds of formula (I), wherein R1, R2, and X are as described in the description and their use as orexin receptor antagonists.

Lithiation-electrophilic substitution of N-thiopivaloylazetidine

(Figure Presented) The fourth protocol: The rarely studied Nthiopivaloyl group plays a crucial role in mediating efficient ∞ lithiation and incorporation of diverse electrophiles onto an azetidine ring; in the presence of chiral ligands, this chemistry also provides the first example of an enantioselective electrophilic substitution on a four-membered ring.

Preparation and characterization of N-(3-pyridinyl) spirocyclic diamines as ligands for nicotinic acetylcholine receptors

Several N-pyridin-3-yl spirobicyclic diamines, designed as conformationally restricted analogs of tebanicline (ABT-594), were synthesized as novel ligands for nicotinic acetylcholine receptors (nAChR). The spirocyclic compounds exhibited weaker binding affinity, than other constrained analogs in accord with a pharmacophore model. Nevertheless, some (1a, 1b) possessed (partial) agonist potencies comparable to nicotine at the α4β2 subtype, but with greatly improved selectivity relative to the α3β4* nAChR.

Synthesis of chiral non-racemic azetidines by lipase-catalysed acetylations and their transformation into amino alcohols: Precursors of chiral catalysts

Azetidinic mono-acetate 7, diol 6b and di-acetate 10a were prepared with high e.e. using PPL-catalysed acetylations. The absolute configurations of all new enantioenriched compounds were assigned by chemical correlation with known compounds. Mono-acetate 7 was then transformed into 30, an amino alcohol of noteworthy potential interest since it represents an interesting precursor for chiral catalysts, such as 32.

Benzazepine and benzothiazepine derivatives

Vasodilating activity is exhibited by compounds having the formula STR1 wherein X can be --S--or --CH2 --; and R2 is STR2 depending upon the definition of X.

A NEW SYNTHESIS OF OPTICALLY ACTIVE 2-METHOXYCARBONYL-4-AZETIDINONE FROM L-AZETIDINE-2-CARBOXYLIC ACID: UTILITY OF RUTHENIUM TETROXIDE OXIDATION

A first transformation of L-azetidine-2-carboxylic acid (1) into optically active monocyclic N-unsubstituted β-lactam, (2S)-2-methoxycarbonyl-4-azetidinone (6), has been developed via ruthenium tetroxide (RuO4) oxidation process.