169032-99-9

Usage

Uses

Used in Pharmaceutical Industry:
(2S,4S)-1-tert-butyl 2-methyl 4-chloropyrrolidine-1,2-dicarboxylate is used as a potential intermediate in the synthesis of pharmaceutical compounds due to its unique structural features and the presence of functional groups that can be further modified or utilized in the development of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, (2S,4S)-1-tert-butyl 2-methyl 4-chloropyrrolidine-1,2-dicarboxylate serves as a versatile building block for the creation of more complex organic molecules. Its specific stereochemistry and functional groups make it a candidate for use in the synthesis of various organic compounds, including those with potential applications in materials science, agrochemicals, or specialty chemicals.

InChI:InChI=1/C11H18ClNO4/c1-11(2,3)17-10(15)13-6-7(12)5-8(13)9(14)16-4/h7-8H,5-6H2,1-4H3/t7-,8-/m0/s1

Upstream product

• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 497-19-8 sodium carbonate 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 

Downstream Products

• 886447-55-8 ethyl [4-[(4S)-chloro-1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate 
• 844476-69-3 (2S,4R)-2-(2,4,5-trifluorobenzyloxymethyl)-4-tritylsulfanylpyrrolidine-1-carboxylic acid 2,3-dihydrobenzo[1,4]dioxin-5-yl ester 
• 393792-62-6 (2S,4R)-2-(2,4,5-trifluorobenzyloxymethyl)-4-tritylsulfanylpyrrolidine-1-carboxylic acid 2-methoxycarbonylphenyl ester 
• 391889-21-7 (2S,4R)-5-propyl-2-[2-(2,4,5-trifluorobenzyloxymethyl)-4-tritylsulfanylpyrrolidin-1-yl]pyrimidine 
• 391889-57-9 (2S,4R)-(2,5-difluorobenzyl)-[1-(5-propylpyrimidin-2-yl)-4-tritylsulfanylpyrrolidin-2-ylmethyl]amine 
• 391889-55-7 (2S,4R)-2-[1-(5-propylpyrimidin-2-yl)-4-tritylsulfanylpyrrolidin-2-ylmethyl]isoindole-1,3-dione 
• 391888-88-3 (2S,4R)-2-(2,4,5-trifluorobenzyloxymethyl)-4-tritylsulfanylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 844476-74-0 (2S,4R)-2-[(2,5-difluorobenzylamino)methyl]-4-tritylsulfanylpyrrolidine-1-carboxylic acid isopropyl ester 
• 844476-70-6 (2S,4R)-4-mercapto-2-(2,4,5-trifluorobenzyloxymethyl)pyrrolidine-1-carboxylic acid 2,3-dihydrobenzo[1,4]dioxin-5-yl ester 
• 391888-89-4 (2S,4R)-2-(2,4,5-Trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidine 
• 393789-23-6 (2S,4R)-4-mercapto-2-(2,4,5-trifluorobenzyloxymethyl)pyrrolidine-1-carboxylic acid 2-methoxycarbonylphenyl ester 
• 391889-54-6 (2S,4R)-[1-(5-propylpyrimidin-2-yl)-4-tritylsulfanylpyrrolidin-2-yl]methanol 
• 391889-56-8 (2S,4R)-[[1-(5-propylpyrimidin-2-yl)-4-tritylsulfanylpyrrolidin-2-yl]methyl]amine 

Relevant academic research and scientific papers

AlkylFluor: Deoxyfluorination of Alcohols

A practical, high-yielding method for the deoxyfluorination of alcohols is presented using AlkylFluor, a novel salt analogue of PhenoFluor. AlkylFluor is readily prepared on multigram scale and is stable to long-term storage in air and exposure to water. The practicality and applicability of this method is demonstrated with a variety of primary and secondary alcohol substrates.

BORONIC ACID DERIVATIVES AND USES THEREOF

This invention is directed to novel Boronic acid derivatives of Formula I, and pharmaceutically acceptable salts, solvate, solvate of the salt and prodrugs thereof, useful in the prevention (e.g., delaying the onset of or reducing the risk of developing) and treatment (e.g., controlling, alleviating, or slowing the progression of) of Age-related Macular Degeneration (AMD) and related diseases of the eye. These diseases include dry-AMD, Wet-AMD, geographic atrophy, diabetic retinopathy, retinopathy of prematurity, polypoidal choroidal vasculopathy, and degeneration of retinal or photoreceptor ceils. The invention disclosed herein is further directed to methods of prevention, slowing the progress of, and treatment of dry -AMD, Wet- AMD, and geographic atrophy, diabetic retinopathy, retinopathy of prematurity, polypoidal choroidal vasculopathy, and degeneration of retinal or photoreceptor cells, comprising: administration of a therapeutically effective amount of compound of the invention. The compounds of the invention are inhibitors of HTRA1. Thus, the compounds of the invention are useful in the prevention and treatment of a wide range diseases mediated (in whole or in part) by HTRA1. The compounds of the invention are also useful for inhibiting HTRA1 protease activity in an eye or locus of an arthritis or related condition.

Synthesis, biological evaluation, and pharmacokinetic study of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives as VLA-4 antagonists

A series of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives were synthesized and evaluated for their activity as VLA-4 antagonists. Of 22 compounds synthesized, 19 compounds showed potent activity with low nanomolar IC50 values. In addition, the representative compounds 11o and 11p with a hydroxy group in the pyrrolidine ring showed moderate plasma clearance in rats (11o, 30 ml/min/kg and 11p, 21 ml/min/kg) and in dogs (11o, 12 ml/min/kg and 11p, 9 ml/min/kg).

Endothelin-converting enzyme-1 inhibition and growth of human glioblastoma cells

Endothelin-1 (ET-1) is mitogenic and/or antiapoptotic in human cancers, and antagonists to ET-1 receptors are under evaluation for cancer treatment. Inhibition of ET-1 activation by the endothelin-converting enzymes 1 a-d (ECE-1a-d; EC 3.4.24.71) represents another approach to block the ET-1 effect in cancer. To evaluate this potential, we synthesized and characterized a series of low nanomolar nonpeptidic thiol-containing ECE-1 inhibitors, and evaluated their effect, as well as the effect of inhibitors for the related metalloproteases neprilysin (NEP; EC 3.4.24.11) and angiotensin-converting enzyme (ACE; EC 3.4.15.1), on human glioblastoma cell growth. Only ECE-1 inhibitors inhibited DNA synthesis by human glioblastoma cells. Exogenous addition of ET-1 or bigET-1 to glioblastoma cells did not counterbalance the growth inhibition elicited by ECE-1 inhibitors, suggesting that ECE-1 inhibitors block the proliferation of human glioblastoma cells most likely via a mechanism not involving extracellular production of ET-1. This class of molecules may thus represent novel therapeutic agents for the potential treatment of human cancer.

Convenient preparation of aryl ether derivatives using a sequence of functionalized polymers

A four-step synthesis to aryl ether derivatives, three of which utilize polymer-supported reagents, has been developed. Supported triphenylphosphine was successfully utilized in two distinct synthetic processes in the first step, whilst supported base and ionic and covalent scavengers were employed to complete the synthesis and purification of the target compounds.

Pyrrolidine derivatives

The present invention relates to pyrrolidine derivatives useful as inhibitors of metalloproteases, e.g. zinc proteases, and which are effective in treating disease states associated with vasoconstriction.

ROMPgel-Supported Triphenylphosphine with Potential Application in Parallel Synthesis

(Equation Presented) ROMPgel-supported triphenylphosphine was synthesized in three steps (67%) from norbornadiene, 4-bromoiodobenzene, and chlorodiphenylphosphine. The supported reagent has a high loading (2.5 mmol/g) and favorable swelling properties in organic solvents. It has been utilized for the conversion of alcohols to halides, the reduction of ozonides, and the isomerization of α,β-acetylenic esters and in the Staudinger reaction. In general, filtration of the resin from the reaction mixtures and evaporation gave the corresponding products in high yield and purity.

PYRROLIDINE COMPOUNDS

The present invention relates to a pyrrolidine compound and pharmaceutically acceptable esters and/or salts thereof. The compounds are useful as inhibitors of metalloproteases, e.g. zinc proteases, particularly zinc hydrolases, and which are effective in

Pyrrolidine derivatives

The present invention relates to pyrrolidine derivatives useful as inhibitors of metalloproteases, e.g. zinc proteases, and which are effective in treating disease states associated with vasoconstriction.

Pyrrolidine derivatives

The present invention relates to pyrrolidine derivatives and dimeric forms and/or pharmaceutically acceptable esters, and/or salts thereof. The compounds are useful as inhibitors of metalloproteases, e.g. zinc proteases, particularly zinc hydrolases, and which are effective in treating disease states are associated with vasoconstriction of increasing occurrences.