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
• Article Data: 13

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

General Description

N-Carbobenzoxy-4-oxo-L-proline is a chemical compound that is commonly used in organic synthesis and peptide chemistry. It is a derivative of L-proline, an amino acid with a unique five-membered ring structure. The N-Carbobenzoxy group acts as a protecting group for the amine moiety of proline, allowing for selective modification of other functional groups within a peptide sequence. N-Carbobenzoxy-4-oxo-L-proline is also used in the synthesis of pharmaceuticals, specifically as a building block for the creation of biologically active peptides. Its versatile reactivity and stability make it a valuable tool in the synthesis of complex organic molecules.

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 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 
• 51-35-4 4R-4-hydroxyproline 
• 501-53-1 benzyl chloroformate 

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 
• 91958-67-7 (R)-4-hydroxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid 
• 197079-48-4 trans-N-(Benzyloxycarbonyl)-4-hydroxy-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.

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.

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.