138923-03-2

Basic information

• Product Name: 2-Cyclopentene-1-carboxylicacid,4-amino-,methylester,(1S,4R)-(9CI)
• Synonyms: 2-Cyclopentene-1-carboxylicacid,4-amino-,methylester,(1S,4R)-(9CI);(1S,4R)-Methyl 4-aMinocyclopent-2-enecarboxylate L-tartrate salt;(1S,4R)-Methyl 4-aMinocyclopent-2-enecarboxylate;Cis-(1S,4R)-4-aMino-2-Cyclopentene-1-carboxylic acid Methyl ester;Methyl (1S,4R)-4-Amino-2-Cyclopentene-1-Carboxylate;methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate
• CAS NO: 138923-03-2
• Molecular Formula: C₇H₁₁NO₂
• Molecular Weight: 141.17
• Product Categories: CARBOXYLICESTER;AMINOACID
• Mol File: 138923-03-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 191.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.109±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 9.66±0.40(Predicted)
• CAS DataBase Reference: 2-Cyclopentene-1-carboxylicacid,4-amino-,methylester,(1S,4R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclopentene-1-carboxylicacid,4-amino-,methylester,(1S,4R)-(9CI)(138923-03-2)
• EPA Substance Registry System: 2-Cyclopentene-1-carboxylicacid,4-amino-,methylester,(1S,4R)-(9CI)(138923-03-2)

Safety Data

• Hazardous Substances Data: 138923-03-2(Hazardous Substances Data)

Usage

Uses

Methyl (1S,4R)-4-Amino-2-Cyclopentene-1-Carboxylate is used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Synthesis

Weigh 50g of the by-product (+)1-amino-4-carboxy-2-cyclopentene extracted by γ-lactam enzymatic resolution and put it in a flask, add 200g of water, and slowly add dropwise at 25~30℃ Sulfuric acid, adjust the pH value of the solution to 1~2, after the dripping is completed, add 0.1g of the racemic catalyst o-phthalaldehyde, then heat to reflux, and react for 10~15h. Concentrate under reduced pressure to no fraction, add 200ml of methanol, 20g of tartaric acid, cool to 10-20°C, filter and wash with methanol. Then add 20g of thionyl chloride and 100ml of methanol to the filter cake, react at 65°C for 8h and concentrate under reduced pressure until there is no fraction. Add 100ml of dichloromethane, stir to dissolve and wash the dichloromethane layer twice with drinking water to obtain (- ) Methyl 1-amino-4-carboxylate-2-cyclopentene in dichloromethane solution, yield 42%.

Upstream product

• 419563-22-7 (1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester tartrate 
• 157732-11-1 (1R,4S)-N-acetoxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 183074-62-6 N-acetoxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 157810-21-4 (1R,4S)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one 
• 157732-10-0 2-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 67-56-1 methanol 
• 102579-71-5 (-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid 

Downstream Products

• 194087-01-9 (1S,3R)-3-Benzyloxymethyl-cyclopentylamine 
• 229613-93-8 (+)-methyl (3aR,4R,6S,6aS)-4-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate 
• 168683-02-1 (1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate 

Relevant articles and documents

Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity

The design and synthesis of novel, orally active, potent, and selective inhibitors of influenza neuraminidase differing structurally from existing neuraminidase inhibitors are described. X-ray crystal structures of complexes of neuraminidase with known five- and six-membered ring inhibitors revealed that potent inhibition of the enzyme is determined by the relative positions of the interacting inhibitor substituents (carboxylate, glycerol, acetamido, hydroxyl) rather than by the absolute position of the central ring. This led us to design potential neuraminidase inhibitors in which the cyclopentane ring served as a scaffold for substituents (carboxylate, guanidino, acetamido, alkyl) that would interact with the four binding pockets of the neuraminidase active site at least as effectively as those of the established six-membered ring inhibitors such as DANA (2), zanamivir (3), and oseltamivir (4). A mixture of the isomers was prepared initially. Protein crystallography of inhibitor - enzyme complexes was used to screen mixtures of isomers in order to identify the most active stereoisomer. A synthetic route to the identified candidate 50 was developed, which featured (3 + 2) cycloaddition of 2-ethylbutyronitrile oxide to methyl (1S,4R)-4[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylate (43). Structures of the synthetic compounds were verified by NMR spectroscopy using nuclear Overhauser effect methodology. Two new neuraminidase inhibitors discovered in this work, 50 and 54, have IC50 values vs neuraminidase from influenza A and B of 50 values are comparable or superior to those for zanamivir and oseltamivir, agents recently approved by the FDA for treatment of influenza. The synthetic route used to prepare 50 and 54 was refined so that synthesis of pure active isomer 54, which has five chiral centers, required only seven steps from readily available intermediates. Further manipulation was required to prepare deoxy derivative 50. Because the activities of the two compounds are comparable and 54 [RWJ-270201 (BCX-1812)] is the easier to synthesize, it was selected for further clinical evaluation.

Access to 1′-Amino Carbocyclic Phosphoramidite to Enable Postsynthetic Functionalization of Oligonucleotides

We report a synthesis of a carbocyclic, abasic RNA phosphoramidite decorated with an amino functionality. The building block was efficiently incorporated into an RNA oligonucleotide in a site-specific manner, followed by deprotection to a free amino group

Substituent and solvent effects in the 1,3-dipolar cycloadditions for synthesis of anti-influenza agent peramivir and its analog

Influenza remains a health problem to humans. Peramivir is a FDA approved anti-influenza drug targeting the virus neuraminidase. The (3 + 2) cycloaddition reaction of 2-ethylbutanenitrile oxide with the cyclopentene dipolarophile derived from Vince lactam is a key step in the conventional synthesis of peramivir. Our study showed that conducting the (3 + 2) cycloaddition reactions with either aliphatic or aromatic nitrile oxide in hexane solution provided high percentage of the desired regioisomer, and the N-substituent having electron-withdrawing property is also beneficial to the regioselectivity. This study also demonstrated an alternative synthetic pathway of (?)-peramivir and the analog having a phenyl group in place of the 3-pentyl moiety.

Process for preparing (-)-(1S, 4R) N-protected 4-amino-2-cyclopentene-1-carboxylate esters

The invention relates to a process for preparing (?)-(1S,4R) N protected 4-amino-2-cylcopentene-1-carboxylate esters represented by the formula (I) wherein R1 and R2 are as described within the specification.