38605-65-1

Usage

InChI:InChI=1/C6H10N2O3/c7-6(11)8-3-1-2-4(8)5(9)10/h4H,1-3H2,(H2,7,11)(H,9,10)/t4-/m0/s1

Upstream product

• 590-28-3 potassium cyanate 
• 609-36-9 rac-Pro-OH 
• 57-13-6 urea 
• 147-85-3 L-proline 
• 578741-04-5 (+/-)-N-carbamoylproline methyl ester 
• 344-25-2 D-Prolin 
• 372-75-8 Citrulline 

Downstream Products

• 578741-04-5 (+/-)-N-carbamoylproline methyl ester 
• 40856-87-9 (S)-tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione 

Relevant academic research and scientific papers

Experimental and theoretical vibrational study of N-carbamoyl-L-proline

The infrared and Raman spectra of N-carbamoyl-L-proline, C6H10N2O3 [(2S)-1-carbamoylpyrrolidine-2-carboxylic acid] were obtained and interpreted with the help of DFT calculations. Six relatively stable molecular conformers were predicted by theory, being one of these similar to the conformer present in the crystal whose X-ray study was already known. The vibrational study was based in that conformer. The experimental vibrational data and assignments were used as basis for the definition of the Scaled Quantum Mechanics (SQM) force field for the molecule. The Potential Energy Distribution (P.E.D.), which revealed the complex nature of many molecular vibrations, and a set of internal force constants were calculated from this SQM force field.

(2S)-1-Carbamoylpyrrolidine-2-carboxylic acid

In the title compound, also known as N-carbamoyl-l-proline, C6H10N2O3, the pyrrolidine ring adopts a half-chair conformation, whereas the carboxyl group and the mean plane of the ureide group form an angle of 80.1 (2)°. Mol-ecules are joined by N - H...O and O - H...O hydrogen bonds into cyclic structures with graph-set R 2 2(8), forming chains in the b-axis direction that are further connected via N - H...O hydrogen bonds into a three-dimensional network. International Union of Crystallography 2007.

2-PYRROLIDINE PHENYLHYDRAZIDES ANTIBACTERIAL AGENTS

2-Pyrrolidine phenylhydrazides antibacterial agents The present invention relates to 2-pyrrolidine phenylhydrazide compounds of formula (I), which are selective antibacterials specifically agalnstAcineto barter baumannii.The invention also relates to their therapeutic use as antibacterials, to a process for their preparation and to pharmaceutical compositions containing them.

Straightforward preparation of labeled potassium cyanate by ozonation and application to the synthesis of [13C] or [14C] ureidocarboxylic acids

The development of new efficient syntheses of labeled reagents is a great challenge. Avoidance of overcomplicated procedures, availability and cost of starting materials are important considerations in choosing the synthetic route. In this report, we desc

Synthesis and crystal structure determination of hydantoin-l-proline

The title compound, hydantoin-l-proline, C6H8N 2O2, crystallize in the orthorhombic system with space group P212121 (N°19), Z = 4, and unit cell parameters a = 7.136(1) A, b = 8.009(2) A, c = 11.378(2) A. The molecular structure shows a hydantoin and pyrrolidine ring coupling forming a bicyclohydantoin. The crystal packing is governed by N-H???O hydrogen bond-type intermolecular interactions, forming infinite one-dimensional chains.

Synthesis, crystal structure and hydrogen-bonding patterns in (RS)-1-carbamoyl pyrrolidine-2-carboxylic acid

The title compound, N-carbamoyl-DL-proline, C6H 10N2O3, crystallizes in the triclinic P-1 space group with unit cell parameters a = 7.610 (4) A, b = 9.259 (5) A, c = 11.749 (7) A, α = 110.294 (11)°, β = 101.304 (13)°, γ = 91.391 (16)°, with two crystallographically independent molecules in the asymmetric unit. The ureido and carboxyl groups are equatorial and axial to the pyrrolidine rings, respectively. The pyrrolidine rings adopt envelope and twisted conformations in the residue A and B, respectively. The molecules are joined by N-H...O and O-H...O hydrogen bonds into cyclic structures with graph set R22(8), forming infinite chains parallel to the cb plane with graph set C22(14), that are further connected via N-H...O hydrogen bonds into a three-dimensional network. Springer Science+Business Media, LLC 2012.

Microwave-assisted synthesis of N-monosubstituted urea derivatives

An easy and rapid procedure for the preparation of N-monosubstituted ureas via reaction between potassium cyanate and a wide range of amines is described. The procedure was performed under microwave irradiation using water as solvent. This methodology is particularly attractive since it provides ureas in high yield and purity. Georg Thieme Verlag Stuttgart · New York.

Rapid and efficient microwave-assisted synthesis of N-carbamoyl-L-amino acids

A rapid and efficient method for the synthesis of N-carbamoyl-L-amino acids is reported. The procedure, involving the reaction between urea and α-amino acids sodium salts, was performed under microwave conditions using an unmodified domestic microwave oven. A careful study of the operative conditions indicated proline (1d) as the less reactive substrate and phenylglycine (1e) as the more reactive one among all the α-amino acids tested. Substitution of urea with potassium cyanate produced a low conversion into the corresponding N-carbamoyl derivative, and a possible explanation of this result is reported. Copyright Taylor & Francis Group, LLC.

Enzyme-catalyzed enantiomeric resolution of N-Boc-proline as the key-step in an expeditious route towards RAMP

For the preparation of both enantiomers of N-carbamoyl-2-methoxymethylpyrrolidine, the precursors of Enders' chiral auxiliaries, SAMP and RAMP, enzyme-catalyzed kinetic resolution of racemic N-carbamoyl, N-Boc, N-Cbz proline esters and prolinols were examined. B. licheniformis protease (subtilisin) preferentially hydrolyzed the (R)-carbamoylproline ester with an enantiomeric ratio (E) of 10. To a hydrophobic N-Cbz proline ester, subtilisin showed lower selectivity (E=2.8), and in contrast, a purified protease (isozyme A) from the earthworm showed the preference of (S)-enantiomer (E=13.6). In a practical sense, C. antarctica lipase B (Chirazyme L-2) was effective for the hydrolysis of both N-Boc and N-Cbz derivatives with E >100. The e.e. of (R)-N-carbamoyl-2-methoxymethylpyrrolidine was raised to be >99.9% by recrystallization at the N-Boc-prolinol stage, which was derived from the (R)-N-Boc-proline methyl ester (98.7% e.e.) through a preparative-scale enzyme-catalyzed resolution (49% yield) of the racemic substrate.

Reactivite du nitrite de sodium. V. Action sur les amino-acides, peptides et proteines

The action of sodium nitrite on various amino-acids was re-examined in conditions approximating to a biological medium. 13C-NMR provides evidence of the existence of intramolecular ring closures and the formation of 5-membered rings with ornithine, citrulline and arginine.The reaction of cystine shows the opening of the sulphur bridges, whereas cysteine leads to the formation of carboxy-thiiran and 3-sulpho-lactic acid.The hydrolysis of the amide bonds of asparagine and glutamine is complete whereas the peptides studied - carnosine and aspartam - do not undergo hydrolysis of the peptide linkage.However, the first deamination of glutathion (γ-Glu-Cys-Gly) induces the peptide link to be broken and a cyclization with the formation of lactone to occur.A second deamination takes place on the cysteinyl residue released and allows the formation of a thiiran by intramolecular cyclization with the thiol group.The formation of thiiran was also observed with oxidized glutathion which has an S-S bridge.Finally, the formation of nitrosamines was detected by 15N-NMR during the reaction of sodium nitrite with two commercial products available to the general public.