72289-52-2

Usage

Functional Groups

Ester, Hydroxyl group, and tert-butyl group

Structure

The compound has a pyrrolidine ring with a hydroxyl group and a tert-butyl group attached to it, and a phenylmethyl ester group at the 1-position.

Stereochemistry

The compound has two chiral centers at the 2nd and 4th positions of the pyrrolidine ring, with the (2S,4R) configuration.

Application

Organic synthesis and pharmaceutical research as a building block for various drugs and pharmaceutical compounds.

Fields of Interest

Medicinal chemistry and drug discovery.

Upstream product

• 147489-27-8 (2S)-4-oxo-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester 
• 224321-02-2 (2S,4R)-4-Acetoxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 501-53-1 benzyl chloroformate 
• 507-19-7 t-butyl bromide 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 64187-47-9 1-benzyloxycarbonyl-4-keto-L-proline 
• 89625-39-8 (2S,4R)-N-(benzyloxycarbonyl)-4-acetoxyproline 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 393154-87-5 ert-butyl 4-hydroxypyrrolidine-2-carboxylate 
• 322398-76-5 N-benzyloxycarbonyl-4-trans-mesyloxy-L-proline tert-butyl ester 
• 147489-27-8 (2S)-4-oxo-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester 
• 654666-04-3 (2S,4R)-4-cyanomethyl-1-phenylmethoxycarbonyl-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 654666-09-8 (2S,4S)-4-cyanomethyl-1-phenylmethoxycarbonyl-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 654666-17-8 (2S,4S)-4-(2-Amino-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 654666-18-9 (2S,4R)-4-(2-Amino-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 1026656-91-6 (2S,4R)-4-(2-Guanidino-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 
• 1026459-86-8 (2S,4S)-4-(2-Guanidino-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 
• 654666-08-7 (2S,4R)-4-(Benzenesulfonyl-cyano-methyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 654666-10-1 (2S,4R)-4-(N,N'-di-tert-butoxycarbonyl-2-guanidinoethyl)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester 
• 654666-05-4 (2S,4S)-4-(N,N'-di-tert-butoxycarbonyl-2-guanidinoethyl)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester 
• 654666-12-3 (2S,4R)-4-(N-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-2-guanidinoethyl)-1-phenylmethoxycarbonyl-pyrrolidine-2-carboxylic acid 
• 654666-07-6 (2S,4S)-4-(N-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-2-guanidinoethyl)-1-phenylmethoxycarbonyl-pyrrolidine-2-carboxylic acid 

Relevant academic research and scientific papers

PROLINE DERIVATIVES FOR USE IN THE TREATMENT OF DIABETES

The present invention provides novel heterocyclic compounds and methods of preparing such compounds. The compounds of the invention are useful for palliative, curative or prophylactic treatment of diseases or conditions of diabetes and/or hypertension. This invention also relates to pharmaceutical compositions containing the compounds of the present invention, and methods for palliative, curative or prophylactic treatment of diseases or conditions of diabetes and/or hypertension. The present invention also provides pharmaceutical compositions consisting of the heterocyclic compounds along with one or more dyslipidemic agents, antiobesity agents, anti-hyperglycemic agents, antihypertensive agents and anti-inflammatory agents.

Restriction of a Peptide Turn Conformation and Conformational Analysis of Guanidino Group Using Arginine-Proline Fused Amino Acids: Application to Mini Atrial Natriuretic Peptide on Binding to the Receptor

Compounds (2S,4S)- and (2S,4R)-4-(2′-guanidinoethyl)proline have been synthesized as a conformationally restricted arginine, Their backbones fit the i + 1 position in a turn, and the side chains are restricted compared to that of arginine. These analogues were incorporated into mini atrial natriuretic polypeptide, which has an important turnlike conformation at Gly6-Arg7-Met8-Asp9. Structural analysis revealed that the size of the conformational space of Arg7 on binding to the receptor was approximately one-third of the entire conformational space.

The synthesis of bicyclic proline derivatives with 1,4N-lactam grouping

The N-benzyloxycarbonyl-4-oxoproline ferr-butyl ester prepared from trans-4-hydroxy-L-proline was shown to be capable of a reductive amination with esters of α- or β-amino acids to the corresponding (45)-4-aminoderivatives. One of the resulting products, (45)-4-glycinoderivative, was easily cyclized after selective removal of the acid-labile protective group. There resulted bridge bicyclic synthons suitable for peptide synthesis: (2S,5S)-benzyloxycarbonyl-4-methoxycarbonylmethyl-3-oxo-1,4-diazabicyclo[2.2.1] heptane, (2S,5S)-1-(9-fluorenylmethoxycarbonyl-4-methoxycarbonyl-3-oxo-1,4- diazabicyclo[2.2.1 ]heptane, and (2S,5S)-1-(9-fluorenylmethoxycarbonyl-4-carboxymethyl-3-oxo-l,4-diazabicyclo[2. 2.1]heptane. Their possible use for the study of biologically significant conformations of bioactive proline-containing oligopeptides is discussed.

Synthesis of conformationally constrained DTPA analogues. Incorporation of the ethylenediamine units as aminopyrrolidines

The synthesis of conformationally constrained diethylenetriaminepentaacetic acid (DTPA) analogues is an effort to probe the relationship between ligand structure and metal complex stability. In the pursuit of this objective, diastereomerically and enantiomerically pure mono- and bis-pyrrolidine analogues of DTPA have been prepared from trans-4-hydroxy-L-proline. The mono-pyrrolidine chelator 1 was constructed from a single hydroxyproline unit and an ethylenediamine moiety while two hydroxyproline-derived fragments 4e or 14b and 9b were coupled by N-alkylation of a triflate to afford the core bis-pyrrolidine structures: optically active 10 and meso-15. Deprotection of the triamine pentaesters 12 and 17 afforded the triamine pentaacetic acids 2 and 3 as their hydrochloride salts. The stereochemical homogeneity of precursor esters 12 and 17 was determined by HPLC using authentic epimeric standards to establish that essentially no racemization of the original amino acid α-center had occurred. Some loss of stereochemical homogeniety was encountered in the synthesis of 10 and 15 by N-alkylation of aminoproline 9b with a hydroxyproline-derived triflate, which had proceeded with some retention of configuration. The diastereomeric impurities were removed by crystallization of the respective benzyl carbamates. Bis-pyrrolidine pentaacids 2 and 3 formed isolable chelates with gadolinium and lutetium. A comparision of the lutetium chelates of 2 and 3 by NMR revealed significant differences which were reflective of a rigid structure with 2, while metal complexation with 3 was structurally less defined.