359849-58-4

Basic information

• Product Name: (1S,2S)-(-)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride
• Synonyms: (1S,2S)-2-AMINO-CYCLOPETANECARBOXYLIC ACID HYDROCHLORIDE SALT ;(1S,2S)-2-amino cyclopetanecarboxylic acid hydrochloride;(1S,2S)-(-)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride;(1S,2S)-2-aminocyclopentanecarboxylicAcidHydrochloride
• CAS NO: 359849-58-4
• Molecular Formula: C6H11NO2.HCl
• Molecular Weight: 165.62
• Mol File: 359849-58-4.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: (1S,2S)-(-)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-(-)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride(359849-58-4)
• EPA Substance Registry System: (1S,2S)-(-)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride(359849-58-4)

Safety Data

• Hazardous Substances Data: 359849-58-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(1S,2S)-(-)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a valuable building block for the development of new drugs and therapeutic agents.
Used in Drug Design and Development:
The stereochemistry of (1S,2S)-(-)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride is of particular interest in drug design and development. Its specific stereoisomerism can influence the pharmacological activity and selectivity of the resulting drug molecules, making it an important factor to consider in the optimization of drug candidates.
Used in Organic Synthesis:
(1S,2S)-(-)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride is used as a versatile reagent in organic synthesis. Its unique functional groups and stereochemistry allow for a wide range of chemical reactions, enabling the synthesis of complex organic molecules with potential applications in various industries.
Used in the Treatment of Medical Conditions:
(1S,2S)-(-)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride has potential applications in the treatment of various medical conditions. Its unique properties and interactions with biological systems make it a promising candidate for the development of novel therapeutic agents.

InChI:InChI=1/C6H11NO2.ClH/c7-5-3-1-2-4(5)6(8)9;/h4-5H,1-3,7H2,(H,8,9);1H/t4-,5-;/m0./s1

Upstream product

• 122672-46-2 (-)-cispentacin 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 359586-68-8 (1S,2S)-2-[(1'S)-phenylethyl]aminocyclopentanecarboxylic acid 
• 1609100-30-2 ethyl cis-2-aminocyclopentane-1-carboxylate 
• 197916-36-2 ethyl (1R,2S)-2-aminocyclopentane-1-carboxylate 
• 1039114-07-2 (1R,2S)-2-Isocyanato-cyclopentanecarboxylic acid methyl ester 
• 592503-41-8 cis-2-acetylaminocyclopentanecarboxylic acid ethyl ester 
• 7149-18-0 ethyl 2-amino-1-cyclopentene-1-carboxylate 
• 142-29-0 cyclopentene 
• 39155-95-8 (1S,5R)-6-azabicyclo<3.2.0>heptan-7-one 
• 179123-04-7 N-hydroxymethyl-6-azabicyclo[3.2.0]heptan-7-one 
• 22031-52-3 2-aza-3-oxobicyclo<3.2.0>heptane 
• 22031-52-3 cis-2-aza-3-oxobicyclo<3.2.0>heptane 
• 179462-33-0 (1S,5R)-6-hydroxymethyl-6-azabicyclo[3.2.0]heptan-7-one 

Downstream Products

• 282524-97-4 rel-(1R,2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}cyclopentanecarboxylic acid 

Relevant articles and documents

The N-Hydroxymethyl Group as a Traceless Activating Group for the CAL-B-Catalysed Ring Cleavage of β-Lactams: A Type of Two-Step Cascade Reaction

An efficient enzymatic two-step cascade procedure has been devised for rapid access to diverse amino acids from N-hydroxymethyl-β-lactams; representative amino acids include the antifungal agent cispentacin, intermediates for the taxol side-chain, and assorted cathepsin inhibitors. When CAL-B-catalysed hydrolyses of racemic N-hydroxymethyl-β-lactams were performed with H2O (0.5 equiv.) in iPr2O at 60 °C, relatively quick (vs. non-activated counterparts) and enantioselective (E > 200) ring cleavage reactions took place. As the ring-opened amino acids formed, the hydroxymethyl group, as a traceless activating group, underwent spontaneous in situ degradation. Consequently, the desired β-amino acid and unreacted N-hydroxymethyl-β-lactam enantiomers (ee > 95 %) were formed. The formation of polymers, induced by liberation of formaldehyde, was successfully restricted by the addition of benzylamine as a capture agent, to the enzymatic reactions. An efficient enzymatic two-step cascade procedure was devised for CAL-B-catalysed hydrolysis of racemic N-hydroxymethyl-β-lactams. Conditions in which the hydroxymethyl group serves as a traceless activating group (E > 200), giving desired β-amino acid along with unreacted starting lactam enantiomers (ee > 95 %) were identified; polymerization was controlled by addition benzylamine addition.

Solid-phase synthesis of 6,7-cycloalkane-fused 1,4-diazepane-2,5-diones via a cyclization/release strategy

A solid-phase synthesis procedure for the parallel preparation of 6,7-cycloalkane-fused 1,4-diazepane-2,5-diones is described. The methodology applies α- and alicyclic β-amino acid building blocks to construct the seven-membered heterocyclic core, while a

Hairpin folding behavior of mixed α/β-peptides in aqueous solution

The invention of new strategies for the design of protein-mimetic oligomers that manifest the folding encoded in natural amino acid sequences is a significant challenge. In contrast to the α-helix, mimicry of protein β-sheets is less understood. We report

New compounds

The present invention encompasses compounds of general formula (1) wherein R1, R2, R4, X, m, n and p are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and their use for preparing a pharmaceutical composition having the above-mentioned properties.

Development of a suitable process for the preparation of a TNF-α converting enzyme inhibitor, WAY-281418

A suitable process for the preparation of kilogram quantities of a TNF-α converting enzyme (TACE) inhibitor (WAY-281418) was developed using isatin 13 as starting material and an efficient coupling step for the formation of sulfonamide 8 in a 15% overall yield. Process preparation of (+)-(1S,2R)-2-aminocyclopentane-1-carboxylic acid (7, (+)-cispentacin), a chiral component for WAY-281418, was successfully scaled up via an asymmetric hydroge-nation reaction. Crystallization allowed the isolation of all intermediates and the final product 9.

NEW COMPOUNDS

The present invention encompassescompounds of general formula (1) wherein R1 to R4 , X and n are defined as in claim 1, which are suitable for the treatment of ailments characterised byexcessive or abnormal cell proliferation, and the use thereof for preparing a medicament having the above-mentioned properties.

The first direct enzymatic hydrolysis of alicyclic β-amino esters: A route to enantiopure cis and trans β-amino acids

The first direct enzymatic method is reported for the synthesis of cis and trans βamino acid enantiomers through the lipase-catalyzed enantioselective hydrolysis of alicyclic β esters in organic media. High enantioselectivities (E usually > 001) were observed when the Candida antarctica lipase B catalyzed reactions were performed with H2O (0.5 equivalents) in iP iPr2O at 5°C. The resolved products, obtained in good yields (≥42%), could be easily separated.

2,4-diamino-pyrimidines as aurora inhibitors

The present invention encompasses compounds of general formula (1) wherein R1 to R3 are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and the use thereof for preparing a pharmaceutical composition having the above-mentioned properties.

Self-condensation of N-tert-butanesulfinyl aldimines: Application to the rapid asymmetric synthesis of biologically important amine-containing compounds

(Chemical Equation Presented) Highly diastereoselective intra- and intermolecular self-condensation reactions of N-tert-butanesulfinyl aldimines have been developed and applied to the rapid, asymmetric synthesis of frans-2-aminocyclopentanecarboxylic acid and the drug candidate SC-53116. Key to both syntheses is a novel microwave-assisted reaction in which N-sulfinyl aldimines are cleanly converted into nitrites in high-yielding concerted elimination processes.

Lipase-catalyzed enantioselective ring opening of unactivated alicyclic-fused beta-lactams in an organic solvent.

[reaction: see text] A highly efficient and very simple method was developed for the synthesis of enantiopure beta-amino acids (e.g. cispentacin) and beta-lactams through the enzyme-catalyzed enantioselective ring opening of unactivated alicyclic beta-lac