71830-08-5

Basic information

• Product Name: (1R,3S)-3-Aminocyclopentanecarboxylic acid
• Synonyms: (-)-(1S,3R)-1-amino-cyclopent-2-ene-4-carboxylic acid ;Cyclopentanecarboxylic acid, 3-amino-, (1R,3S)- (9CI);(1R,3S)-3-Aminocyclopentanecarboxylic acid, 98% ee, 95%;(-)-(1R,3S)-b-Homocycloleucine;(1R,3S)-3-Aminocyclopentanecarboxylic acid, 95%, ee:98%;(1R,3S)-3-Aminocyclopentanecarboxylic acid,95%,98% ee;(-)-(1R,3S)-3-Aminocyclopentanecarboxylic acid ,99%;(1R,3S)-3-AMinocyclopentane-1-carboxylic
• CAS NO: 71830-08-5
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• Product Categories: AMINOACID;Unusual amino acids;API intermediates
• Mol File: 71830-08-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 172.1 °C
• Boiling Point: 239.22°C (rough estimate)
• Flash Point: 113.9 °C
• Appearance: Off-white to beige/Crystalline Powder
• Density: 1.1426 (rough estimate)
• Vapor Pressure: 0.00278mmHg at 25°C
• Refractive Index: 1.4300 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 4.44±0.20(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Air Sensitive
• CAS DataBase Reference: (1R,3S)-3-Aminocyclopentanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3S)-3-Aminocyclopentanecarboxylic acid(71830-08-5)
• EPA Substance Registry System: (1R,3S)-3-Aminocyclopentanecarboxylic acid(71830-08-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 22-26-36/37/39
• Hazardous Substances Data: 71830-08-5(Hazardous Substances Data)

Usage

Description

(1R,3S)-3-Aminocyclopentane carboxylic acid is a synthetic intermediate useful for pharmaceutical synthesis.

Chemical Properties

off-white to beige crystalline powder

Uses

Different sources of media describe the Uses of 71830-08-5 differently. You can refer to the following data:
1. (1R,3S)-(-)-3-Aminocyclopentanecarboxylic acid is used as pharmaceutical intermediate.
2. (1R,3S)-3-Aminocyclopentanecarboxylic Acid is used in the synthesis of aminocyclopentanecarboxylic acid-containing cyclic RGD peptides. It is also used to prepare BMS-457, a potent and selective CCR1 antagonist.

InChI:InChI=1/C6H11NO2/c7-5-2-1-4(3-5)6(8)9/h4-5H,1-3,7H2,(H,8,9)/t4-,5+/m1/s1

Upstream product

• 24647-29-8 2-Azabicyclo[2.2.1]heptan-3-one 
• 49805-30-3 racemic 2-azabicyclo[2.2.1]hept-5-en-3-one 
• 74201-94-8 methyl 3-(N-benzyloxycarbonylamino)cyclopent-1-ene-1-carboxylate 
• 74201-88-0 3-aminocyclopent-1-ene-1-carboxylic acid 
• 74201-92-6 3-bromocyclopent-1-ene-1-carbonitrile 
• 3047-38-9 cyclopent-1-enecarbonitrile 
• 102579-71-5 cis-4-amino-cyclopent-2-ene-1-carboxylic acid 
• 49805-27-8 3-tosyl-2-azabicyclo [2.2.1]hepta-2,5-diene 
• 714195-06-9 methyl 3-aminocyclopentane-1-carboxylate 
• 96443-42-4 (+)-cis-(1S,3R)-3-carbomethoxycyclopentane carboxylic acid 

Downstream Products

• 1312023-76-9 ethyl (1R,3S)-3-[4-(N-hydroxycarbamimidoyl)phenylamino]cyclopentanecarboxylate 
• 1398512-07-6 C₂₄H₂₉ClN₄O₅ 
• 1431568-43-2 tert-butyl (1S,3S)-3-{(2-acetamido-1-(tert-butylamino)-1-oxo-hex-5-en-2-yl)cyclopentyl-[1,1'-biphenyl]-4-ylmethyl}-carbamate 
• 1431568-42-1 tert-butyl (1S,3S)-3-{(2-acetamido-1-(tert-butylamino)-1-oxo-hex-5-en-2-yl)cyclopentyl-[1,1'-biphenyl]-4-ylmethyl}-carbamate 
• 1431568-41-0 tert-butyl ([1,1'-biphenyl]-4-ylmethyl)((1S,3R)-3-(pent-4-enoyl)cyclopentyl)carbamate 
• 1431568-40-9 tert-butyl-[1,1'-biphenyl]-4-ylmethyl-{(1S,3R)-3-(methoxy(methyl)carbamoyl)-cyclopentyl}-carbamate 
• 1431568-39-6 (1R,3S)-3-((biphenyl-4-ylmethyl)(tert-butoxycarbonyl)amino)cyclopentane carboxylic acid 
• 1418200-51-7 ((1S,3R)-3-[6-benzenesulfonyl-2-((R)-1-hydroxyethyl)-6H-1,3,5,6-tetraaza-as-indacen-1-yl]-cyclopentyl)-acetonitrile 
• 1418200-20-0 ((1S,3R)-3-(6-benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6H-1,3,5,6-tetraaza-as-indacen-1-yl)-cyclopentyl)-acetonitrile 
• 1418200-12-0 ((1R,3S)-3-[6-benzenesulfonyl-2-((R)-1-hydroxy-ethyl)-6H-1,3,5,6-tetraaza-as-indacen-1-yl]-cyclopentyl)-acetonitrile 
• 1418200-11-9 ((1R,3S)-3-(6-benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6H-1,3,5,6-tetraaza-as-indacen-1-yl)-cyclopentyl)-acetonitrile 
• 1418200-42-6 toluene-4-sulfonic acid (1R,3S)-3-(6-benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6H-1,3,5,6-tetraaza-as-indacen-1-yl)-cyclopentylmethyl ester 
• 1418200-10-8 ((1R,3S)-3-(6-benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6H-1,3,5,6-tetraaza-as-indacen-1-yl)-cyclopentyl)-methanol 
• 1418200-09-5 (1R,3S)-3-(6-benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6H-1,3,5,6-tetraaza-as-indacen-1-yl)-cyclopentanecarboxylic acid methyl ester 

Relevant articles and documents

Enhanced enzymatic synthesis of the enantiopure intermediate for the blockbuster drug intermediate abacavir through a two-step enzymatic cascade reaction

A very efficient enzymatic two-step cascade reaction was devised (E?>?200) for the resolution of activated γ-lactams (±)-1 and (±)-2. The N-hydroxymethyl group worked as a traceless activating group, when the reactions were performed with H2O (0.5?equiv) in the presence of benzylamine (1?equiv) in i-Pr2O at 60?°C. The ring-opened enantiomerically pure γ-amino acids (1S,4R)-6 (ee?=?99%, intermediate of abacavir) and (1S,3R)-8 (ee?=?99%) and unreacted lactams (1S,4R)-1 and (1R,4S)-2 (ee???96%) were obtained in good yields (?43%). Treatment of (1S,4R)-1 and (1R,4S)-2 with 18% HCl or NH4OH resulted in (1R,4S)-6·HCl and (1S,3R)-8·HCl or (1S,4R)-3 and (1R,4S)-4 quantitatively, with ee???96%.

Enzymatic method for the synthesis of blockbuster drug intermediates - Synthesis of five-membered cyclic γ-amino acid and γ-lactam enantiomers

A very efficient enzymatic method was developed for the synthesis of cyclic γ-lactam and γ-amino acid enantiomers, intermediates for drugs with a prominent turnover (e.g., abacavir and carbovir), through the CAL-B-catalysed enantioselective (E > 200) hydrolysis of the corresponding N-Boc protected and unprotected racemic γ-lactams with H2O in iPr2O. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthesis of analogues of GABA. XV. Preparation and resolution of some potent cyclopentene and cyclopentane derivatives

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