75857-94-2

Usage

Chemical class

Pyrrolidine carboxylic acids

Ester of

1,2-Pyrrolidinedicarboxylic acid

Contains

Methyl group and phenylmethyl group

Optical activity

(S)configuration

Potential applications

Pharmaceutical industry

Possible uses

Ingredient in drug formulations or building block for synthesizing other compounds

Further research needed

To fully understand properties and potential uses

Upstream product

• 5211-23-4 N-carbobenzyloxy-L-proline methyl ester 
• 501-53-1 benzyl chloroformate 
• 4931-66-2 methyl (S)-pyroglutamate 
• 13907-82-9 N²-benzyloxycarbonyl-L-glutamine methyl ester 
• 5672-83-3 Z-L-GluOMe 
• 31139-36-3 dibenzyl dicarbonate 
• 98-79-3 L-Pyroglutamic acid 
• 147-85-3 L-proline 
• 32159-21-0 Cbz-L-pGlu-OH 
• 74-88-4 methyl iodide 

Downstream Products

• 138-15-8 l-glutamic acid hydrochloride 
• 141406-83-9 methyl (2S)-2-[N-(benzyloxycarbonyl)amino]-5-(hydroxy)pentanoate 
• 93271-97-7 1-benzyl 2-methyl (2S)-5-hydroxypyrrolidine-1,2-dicarboxylate 
• 4931-66-2 methyl (S)-pyroglutamate 
• 257293-94-0 (2S)-4-[2-(3,4-dimethoxyphenyl)ethylcarbamoyl]-2-(benzyloxycarbonyl)aminobutyric acid methyl ester 
• 257293-96-2 (2S)-4-[2-(phenyl)ethylcarbamoyl]-2-(benzyloxycarbonyl)aminobutyric acid methyl ester 
• 257293-99-5 (5S)-5-(benzyloxycarbonyl)amino-1-[2-(3,4-dimethoxyphenyl)ethyl]-6-hydroxypiperidin-2-one 
• 257294-01-2 (1S,12bS)-1-(benzyloxycarbonyl)amino-1,2,3,6,7,11b-hexahydro-9,10-dimethoxybenzo[a]quinolizin-4-one 
• 280765-84-6 [3β(S),5β,12α]-3-[[5-methoxy-1,5-dioxo-4-[[(phenylmethoxy)carbonyl]amino]pentyl]amino]-12-hydroxycholan-24-oic acid methyl ester 
• 1071912-21-4 (2S)-2-benzyloxycarbonylamino-5-oxononanoic acid methyl ester 
• 119813-69-3 methyl (2S)-2-(benzyloxycarbonylamino)-6-(t-butoxycarbonyl)-5-oxohexanoate 
• 119813-70-6 (S)-6-Benzyloxycarbonylamino-2-ethyl-3-oxo-heptanedioic acid 1-benzyl ester 7-methyl ester 
• 116894-75-8 (2S,5S)-5-(1-Benzyloxycarbonyl-2-oxo-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 214072-10-3 (5S)-2-Methoxy-1-[(benzyloxy)carbonyl]-5-methoxycarbonylpyrrolidine 

Relevant academic research and scientific papers

Synthesis of highly functionalized 2,5-disubstituted pyrrolidines via an aza-Morita-Baylis-Hillman-type reaction

An aza-Morita-Baylis-Hillman-type reaction of Michael acceptors with 5-substituted cyclic N,O-acetals derived from pyrrolidines has been investigated. It has been found that the combination of Me2S and TMSOTf work well with unhindered and reactive enals and enones whilst the use of quinuclidine and TMSOTf is superior for more hindered Michael acceptors. The reactions lead to 2,5-trans-disubstituted pyrrolidines with good to excellent diastereoselectivity. The origin of the selectivity is discussed.

Synthesis, determination of the absolute stereochemistry, and evaluations at the nicotinic acetylcholine receptors of a hydroxyindolizidine alkaloid from the ant Myrmicaria melanogaster

The first chiral synthesis of new hydroxyindolizidine alkaloid (1) detected in the ant Myrmicaria melanogaster has been achieved, and its absolute stereochemistry was determined to be 3S, 5R, 8S, 9S by the present chiral synthesis.

Scale-up of trisodium [(3Β,5Β,12α)-3-[[4(S)-4-[bis[2- [bis[(carboxy-kO)methyl]aminokN] ethyl]amino-kN]-4-(carboxy-kO)-1-oxobutyl] amino]-12-hydroxycholan-24- oato(6-)]gadolinate(3-)], a Gd(III) complex under development as a contrast agent for MRI coronary angiography

Process chemistry involved in the discovery and development routes to trisodium [(3Β,5Β,12α)-3-[[4(S)-4-[bis[2-[bis[(carboxykO) methyl]amino-kN]ethyl]amino-kN]-4-(carboxy-kO)-1-oxobutyl]- amino]-12- hydroxycholan-24-oato(6-)]gadolinate(3-)] (B22956/1) starting from L-glutamic acid and (3α,5Β,12α)-3,12-dihydroxycholan-24-oic acid is described. The best process is based on seven chemical steps and overcomes difficult purification protocols. Such process has been successfully implemented to prepare multikilogram batches of the target compound in 20% overall yield from (3α,5Β,12α)-3,12-dihydroxycholan-24-oic acid.

First enantioselective synthesis of a hydroxyindolizidine alkaloid from the ant Myrmicaria melanogaster

The first enantioselective synthesis of the recently reported ant alkaloid 1 has been achieved starting from commercially available lactam 3 in seven steps and 25% overall yield. The proposed structure of the natural product was confirmed by comparison with synthetic 1 and its absolute configuration established as 3S,5R,8S,9S. Georg Thieme Verlag Stuttgart.

Blood pool agents for nuclear magnetic resonance diagnostics

The present invention relates to bile acid conjugates and complexes thereof with gadolinium or manganese ions and the salts thereof with physiologically compatible organic or inorganic bases, a process for the preparation thereof and contrastographic diagnostic pharmaceutical compositions containing them.

Synthesis of [6-13C]-L-lysine

A short and efficient enantioselective synthesis of [6-13C]-L-lysine from commercially available N-benzyloxycarbonyl-L-glutamic acid α-methyl ester is described using [13C]-sodium syanide as the source of isotopic label.

An efficient route to the α-methyl ester of L-glutamic acid, and its conversion into cis-5-hydroxy-L-pipecolic acid

The treatment of the N-benzyloxycarbonyl α-methyl esters of L-glutamine or L-asparagine with tert-butyl nitrite in refluxing acetonitrile results in selective hydrolysis of the amide group, giving optically pure Z-Glu-OMe (74%) or Z-Asp-OMe (88%); these are versatile chiral building blocks, and an efficient synthesis of cis-5-hydroxy-L-pipecolic acid from Z-Glu-OMe is described.

A convenient N-protection of pyroglutamate derivatives

Esters of pyroglutamic acid were N-protected by conventional protective groups (Z. Boc, and COOMe) in high yield, without racemization, using LiHMDS in THF at -78°C and ZCl, Boc2O, and ClCOOMe, respectively.