64187-47-9

Basic information

• Product Name: N-CARBOBENZOXY-4-OXO-L-PROLINE
• Synonyms: N-CARBOBENZOXY-4-OXO-L-PROLINE;N-carbobenzyloxy-4-keto-L-proline;Carbobenzoxyoxoproline;(S)-1-((Benzyloxy)carbonyl)-4-oxopyrrolidine-2-carboxylic acid;1-(Benzyloxycarbonyl)-4-keto-(S)-proline;(S)-1-Z-4-oxopyrrolidine-2-carboxylic acid ;(2S)-4-oxo-1,2-Pyrrolidinedicarboxylic acid 1-(phenylmethyl) ester;1-Benzyloxycarbonyl-4-oxo-L-proline
• CAS NO: 64187-47-9
• Molecular Formula: C₁₃H₁₃NO₅
• Molecular Weight: 263.25
• Mol File: 64187-47-9.mol

Chemical Properties

• Melting Point: 95℃
• Boiling Point: 488.455 °C at 760 mmHg
• Flash Point: 249.209 °C
• Appearance: White to yellow to brown/Powder
• Density: 1.409 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-CARBOBENZOXY-4-OXO-L-PROLINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CARBOBENZOXY-4-OXO-L-PROLINE(64187-47-9)
• EPA Substance Registry System: N-CARBOBENZOXY-4-OXO-L-PROLINE(64187-47-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 64187-47-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-Carbobenzoxy-4-oxo-L-proline is utilized as a key intermediate in organic synthesis for its ability to protect the amine group of proline, enabling chemists to selectively modify other functional groups in complex organic molecules.
Used in Peptide Chemistry:
In peptide chemistry, N-Carbobenzoxy-4-oxo-L-proline is employed as a protecting agent for the amine moiety, allowing for the controlled synthesis of peptides with specific sequences and functionalities.
Used in Pharmaceutical Synthesis:
N-Carbobenzoxy-4-oxo-L-proline is used as a building block in the synthesis of pharmaceuticals, particularly for the creation of biologically active peptides that have potential therapeutic applications.
Used in the Development of Drug Delivery Systems:
N-Carbobenzoxy-4-oxo-L-proline may also be involved in the development of drug delivery systems, where its protective properties can be leveraged to improve the stability and bioavailability of peptide-based drugs.

InChI:InChI=1/C13H13NO5/c15-10-6-11(12(16)17)14(7-10)13(18)19-8-9-4-2-1-3-5-9/h1-5,11H,6-8H2,(H,16,17)/t11-/m0/s1

Upstream product

• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 501-53-1 benzyl chloroformate 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 4347-18-6 4-oxo-L-proline 
• 13504-86-4 (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline 
• 16217-15-5 1-benzyloxycarbonyl-4-oxo-L-proline methyl ester 
• 83507-89-5 N-<(phenylmethoxy)carbonyl>-4-oxo-(S)-proline ethyl ester 
• 81653-75-0 N-(benzyloxycarbonyl)-4-(phenylmethylidene)-L-proline 
• 78464-03-6 N-(benzyloxycarbonyl)-cis-4-hydroxy-trans-4-phenyl-L-proline 
• 75776-49-7 7-aza-1,4-dioxaspiro<4.4>nonane-7,8-dicarboxylic acid 7-(phenylmethyl ester) 
• 75776-77-1 7-<(phenylmethoxy)carbonyl>-1,4-dithia-7-azaspiro<4.4>nonane-8(S)-carboxylic acid 
• 101250-61-7 (S)-2-((S)-1-tert-Butoxycarbonylmethylsulfanylmethyl-3-methyl-butylcarbamoyl)-4-oxo-pyrrolidine-1-carboxylic acid benzyl ester 
• 75776-55-5 N-(benzyloxycarbonyl)-4,4-dimethoxy-L-proline 
• 147489-27-8 (2S)-4-oxo-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 785001-74-3 cis-4-cyclohexyl-L-proline 
• 113949-56-7 trans-1-{[hydroxy(4-phenylbutyl)phosphinyl]acetyl}-4-phenyl-L-proline 

Relevant articles and documents

Preparation method of intermediate

The invention relates to a preparation method of an intermediate, and belongs to the field of medicinal chemistry. The preparation method comprises at least one reaction step of an addition elimination reaction, a cyclization reaction, a reduction reaction, a decarboxylation reaction and a hydrogenation reaction. According to the method disclosed by the invention, the target intermediate with a single configuration can be simply and conveniently obtained, chiral resolution is effectively avoided, the yield is improved, the cost is reduced, and industrial production is facilitated.

Synthesis of 4 - oxo - L - proline derivatives (by machine translation)

The invention relates to the field of preparation methods of chemical drug intermediates, in particular to a method for synthesizing a 4-oxo-L-proline derivative. The method comprises steps as follows: L-hydroxyproline and an oxidant are mixed, and a mixture is obtained and reacts to produce an intermediate product; after an amino-group protective agent is added to a solution containing the intermediate product, the mixture reacts continuously; then, the mixture has a quenching reaction and is subjected to acidification, extraction, separation, drying and purification, and the 4-oxo-L-proline derivative is obtained. According to the method for synthesizing the 4-oxo-L-proline derivative, the primary raw material L-hydroxyproline is low in cost and easy to obtain; the whole synthesizing steps are convenient, simple and easy to operate; poisonous reagents such as heavy metals and the like are not used in the production process, and the 4-oxo-L-proline derivative is environment-friendly, low in cost and suitable for industrial production.

An improved, scalable synthesis of bis-amino acids

trans-4-Hydroxy-L-proline derived bis-amino acids are chiral, cyclic building blocks that display two alpha-amino acids that are differentiated from each other with protecting groups. They are assembled into spiroligomers—rigid, shape-programmable spirocyclic oligomers that are both stereochemically and functionally diverse. The synthesis presented here focuses on recent improvements that allow for a convenient, large-scale synthesis of twelve stereochemically pure bis-amino acids from inexpensive trans-4-hydroxy-L-proline. The bis-amino acids differ in stereochemistry as well as the amine protecting group, one of which (para-nitrobenzyl carbamate) has not been previously incorporated into bis-amino acids.

Synthesis and evaluation of conformationally restricted inhibitors of aspartate semialdehyde dehydrogenase

Inhibitors of the enzyme aspartate semialdehyde dehydrogenase, a key biological target for the generation of a new class of antibiotic compounds, have been developed. To investigate improvements to binding within an inhibitor series, the lowering of the entropic barrier to binding through conformational restriction was investigated. A library of linear and cyclic substrate analogues was generated and computational docking used to aid in structure selection. The cyclic phosphonate inhibitor 18 was thus identified as complimentary to the enzyme active-site. Synthesis and in vitro inhibition assay revealed a K i of 3.8 mM against natural substrate, where the linear analogue of 18, compound 15, had previously shown no inhibitory activity. Two further inhibitors, phosphate analogue diastereoisomers 17a and 17b, were synthesised and also found to have low millimolar Ki values. As a result of the computational docking investigations, a novel substrate binding interaction was discovered: hydrogen bonding between the substrate (phosphate hydroxy-group as the hydrogen bond donor) and the NADPH cofactor (2′-oxygen as the hydrogen bond acceptor). The Royal Society of Chemistry 2011.

Convenient synthesis and evaluation of biological activity of benzyl (2S)-2-[(R)-1-hydroxy-2-oxo-(1-phenethyl)prop-3-ylcarbamoyl]-4-oxopiperidine- (or -4-oxopyrrolidine)-1-carboxylate as novel histone deacetylase inhibitors

A simple synthesis, involving a key coupling reaction, and the biological activity of the title compounds 16 and 17 are described. The key fragments are the amine·HCl salt 6 and the acids 9 and 13, which were smoothly coupled by using ethyl(dimethylaminopropyl)carbodiimide (EDCI) and 1- hydroxybenzotriazole (HOBt) in high yield. We have found that the in vitro growth inhibitory potency of the new compounds 16 and 17 exhibits good histone deacetylase (HDAC) activity.

Diastereoselective synthesis of (2S,5S)- and (2S,5R)-N-benzyloxycarbonyl-5-hydroxypipecolic acids from trans-4-hydroxy-l-proline

An efficient diastereoselective synthesis of cis- and trans-5-hydroxy-(2S)-N-benzyloxycarbonyl pipecolic acids, starting from trans-4-hydroxy-l-proline is described. The key synthetic strategies involve the regioisomeric ring expansion of keto ester 8 and diastereoselective reduction of ketone 11 in high selectivity and yield.

Bis (amino acid) molecular scaffolds

The present invention provides molecular building blocks of rigid bis(amino acids). The molecular building blocks can be linked together through the formation of rigid diketopiperazine rings, to provide the desired three dimensional structure. Also provided is method of synthesizing macromolecules from the bis (amino acid) building blocks.

The synthesis of functionalized nanoscale molecular rods of defined length

We report a synthetic approach to spiro-ladder oligomers of defined length and structure that form water-soluble molecular rods. We describe the synthesis of a chiral molecular building block 1 and its assembly on solid support to form flexible chains that were then rigidified by the parallel formation of several diketopiperazine rings. Two molecular rods approximately 15 and 25 A in length were synthesized containing three and five monomers, respectively. The molecular rods were easily functionalized on both ends and were shown to have high water solubility, making them compatible with biological buffers. These molecules may find use as scaffolds for the display of ligands in chemical-biology applications and as spacers and construction materials for nanoscience applications. Copyright

Aromatic amidine derivatives useful as selective thrombin inhibitors

The present invention relates to a novel thrombin inhibitor which is effective even when orally administered. More specifically, the present invention relates to an aromatic amidine derivative represented by formula (I) and the salts thereof, which show potent selective inhibitory activity for thrombin in which (a), R, R1, R2, R3, A, W, Y and n are defined as described in the specification.

Stereoselective synthesis of novel chimerical amino acids via a photochemical key step

The synthesis of novel chimerical amino acid derivatives 6-8 bearing the 6-azatricyclo[3.3.1.033,7]nonane (methanotropane) skeleton is described. Starting with one chirality centre in L-4-oxoprolines 2 we succeeded in the fully stereoselective introduction of four new chirality centres. The key step of our synthetic route is a photochemical cyclization of phenyl ketones, whose stereoselectivity has been explained by the different stability of the triplet biradical conformers.