207729-00-8

Basic information

• Product Name: Ethyl 1-(Boc-aMino)-3-cyclopentenecarboxylate
• Synonyms: Ethyl 1-(Boc-aMino)-3-cyclopentenecarboxylate;ethyl N-(tert-butoxycarbonyl)-1-amino-cyclopent-3-enecarboxylate
• CAS NO: 207729-00-8
• Molecular Formula: C₁₃H₂₁NO₄
• Molecular Weight: 255.31014
• Mol File: 207729-00-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Ethyl 1-(Boc-aMino)-3-cyclopentenecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 1-(Boc-aMino)-3-cyclopentenecarboxylate(207729-00-8)
• EPA Substance Registry System: Ethyl 1-(Boc-aMino)-3-cyclopentenecarboxylate(207729-00-8)

Safety Data

• Hazardous Substances Data: 207729-00-8(Hazardous Substances Data)

Usage

General Description

Ethyl 1-(Boc-amino)-3-cyclopentenecarboxylate is a chemical compound used in organic synthesis. It is an ester derivative of cyclopentenecarboxylic acid, with an added Boc-protected amino group at the 1-position. The Boc-protected amino group is commonly used in peptide synthesis to protect the amine group during chemical reactions. Ethyl 1-(Boc-aMino)-3-cyclopentenecarboxylate can also be used as a building block for the synthesis of pharmaceuticals and other biologically active molecules. Its unique structure and functional groups make it a valuable tool for chemical research and drug development.

Upstream product

• 71432-55-8 2-tert-butyl-1,3-diisopropylisourea 
• 24424-99-5 di-tert-butyl dicarbonate 
• 199532-88-2 ethyl 1-aminocyclopent-3-ene-1-carboxylate 
• 75-65-0 tert-butyl alcohol 
• 199532-83-7 ethyl 1-((4-bromobenzylidene)amino)cyclopent-3-ene-1-carboxylate 
• 76910-08-2 cyclopent-3-ene-1,1-dicarboxylic acid ethyl ester 
• 76910-09-3 ethyl 1-(chloroformyl)cyclopent-3-ene-1-carboxylate 
• 952193-55-4 (2R)-5,5-diallyl-3,6-diethoxy-2,5-dihydro-2-isopropylpyrazine 
• 952193-54-3 (2R,5S)-5-allyl-3,6-diethoxy-2,5-dihydro-2-isopropylpyrazine 
• 952193-59-8 C₁₅H₂₄N₂O₂ 

Downstream Products

• 213316-20-2 1-(tert-butoxycarbonylamino)-3-cyclopentene-1-carboxylic acid 
• 354526-96-8 N-[(1-(tert-butoxycarbonylamino)-cyclopent-3-enyl)carbonyl]-L-phenylalanine methyl ester 
• 1310415-39-4 C₁₄H₁₅NO₄S 
• 1310417-87-8 C₁₄H₁₅NO₅S 
• 1310415-41-8 C₁₇H₂₃NO₅SSi 
• 1310415-42-9 1-tosyl-3-oxa-1-azaspiro[4.4]non-8-ene-2,7-dione 

Relevant articles and documents

Synthesis of isoxazoline-substituted symmetrical diketopiperazines

A synthesis of racemic isoxazoline substituted symmetrical diketopiperazines has been achieved by twice utilizing a diastereoselective 1,3-dipolar cycloaddition step - mediated by intermolecular hydrogen-bonds between the Boc-NH of 2 and the requisite nitrile oxide (RCN+-O-) - to control alkene face selectivity. Dehydrative cyclization of the amide-linked amino acid 6 delivered diketopiperazine 8.

Synthesis, Radiolabeling, and Biological Evaluation of the cis Stereoisomers of 1-Amino-3-Fluoro-4-(fluoro-18F)Cyclopentane-1-Carboxylic Acid as PET Imaging Agents

The non-natural cyclic amino acids (1S,3R,4S)-1-amino-3-fluoro-4-(fluoro-18F)cyclopentane-1-carboxylic acid ([18F]9) and (1S,3S,4R)-1-amino-3-fluoro-4-(fluoro-18F)cyclopentane-1-carboxylic acid ([18F]28) have been prepared in 10 and 1.7% decay corrected radiochemical yield, respectively, and in greater than 99% radiochemical purity. Cell assays in rat 9L gliosarcoma, human U87 ΔEGFR glioblastoma, and human DU145 androgen-independent prostate carcinoma tumor cells indicated that both compounds are substrates for amino acid transport primarily by system L, with some transport taking place via system ASC. In rats with 9L gliosarcoma, [18F]9 and [18F]28 provided high tumor to normal brain tissue ratios, with maximal ratios of 3.5 and 4.1, respectively. Biodistribution studies in healthy rats confirmed that both compounds are BBB permeable and that bladder accumulation is low until at least 5 min post injection.

Microwave assisted synthesis of spiro-2,5-diketopiperazines

A general and efficient method for the synthesis of spiro-2,5-diketopiperazines (spiro-DKPs) is described. Cyclization of Boc-protected dipeptides containing spiro-amino acids by microwave assisted heating in water furnished the corresponding spiro-DKPs. The spiro-amino acids were prepared by combining stereoselective alkylation reactions using the Sch?llkopf methodology for amino acid construction with Grubbs ring-closing metathesis (RCM) methodology using ruthenium complexes. The RCM reactions and all subsequent transformations to the spiro-DKPs were run with microwave assisted heating, resulting in high yields and short reaction times for all steps.