214206-61-8

Basic information

• Product Name: 2-(TERT-BUTOXYCARBONYLAMINO)HEX-5-ENOIC ACID
• Synonyms: 2-(Boc-amino)-5-hexenoic acid;2-(TERT-BUTOXYCARBONYLAMINO)HEX-5-ENOIC ACID
• CAS NO: 214206-61-8
• Molecular Formula: C₁₁H₁₉NO₄
• Molecular Weight: 229.274
• Mol File: 214206-61-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 369.15°C at 760 mmHg
• Flash Point: 177.056°C
• Appearance: /
• Density: 1.079g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.473
• Storage Temp.: 2-8°C
• PKA: 3.96±0.10(Predicted)
• CAS DataBase Reference: 2-(TERT-BUTOXYCARBONYLAMINO)HEX-5-ENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(TERT-BUTOXYCARBONYLAMINO)HEX-5-ENOIC ACID(214206-61-8)
• EPA Substance Registry System: 2-(TERT-BUTOXYCARBONYLAMINO)HEX-5-ENOIC ACID(214206-61-8)

Safety Data

• Hazardous Substances Data: 214206-61-8(Hazardous Substances Data)

Usage

General Description

2-(tert-butoxycarbonylamino)hex-5-enoic acid is a chemical compound with the molecular formula C11H19NO4. It is a derivative of the amino acid glutamic acid and is commonly used in organic synthesis and drug development. The compound is a white crystalline solid at room temperature and is stable under normal conditions. It has been widely studied for its potential pharmacological properties and has shown promise in the development of new pharmaceuticals. Additionally, 2-(tert-butoxycarbonylamino)hex-5-enoic acid has been used as a building block in the synthesis of various bioactive molecules and as a reagent in organic chemistry reactions. Overall, this compound has significant potential for various applications in the pharmaceutical and chemical industries.

InChI:InChI=1/C11H19NO4/c1-5-6-7-8(9(13)14)12-10(15)16-11(2,3)4/h5,8H,1,6-7H2,2-4H3,(H,12,15)(H,13,14)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 16258-05-2 D,L-2-amino-5-hexenoic acid 
• 756498-97-2 (RS)-ethyl 2 N-(tert-butoxycarbonyl)-2-amino-5-hexenoate 
• 912651-56-0 ethyl 2-N-(diphenylmethyleneamino)hex-5-enoate 
• 360059-80-9 ethyl 2-aminohex-5-enoate 
• 122471-00-5 acetylamino-3-butenyl-propanedioic acid diethyl ester 
• 141943-64-8 (±)-2-acetamidohex-5-enoic acid 
• 92136-57-7 methyl 2-[(tert-butoxycarbonyl)amino]hex-5-enoate 
• 1237001-51-2 2-amino-hex-5-enoic acid hydrochloride 

Downstream Products

• 151294-93-8 (+/-)-tert-butyl 2-[(tert-butoxycarbonyl)amino]-5-hexenoate 
• 1085406-15-0 tert-butyl 1-(((S,Z)-3-(3-(methoxymethoxy)phenyl)-1-(tert-butyldimethylsilyl)allyloxy)carbonyl)pent-4-enylcarbamate 
• 1204324-84-4 tert-butyl 1-(((Z)-3-(3-methoxyphenyl)-1-(tert-butyldimethylsi-lyl)allyloxy)-carbonyl)pent-4-enylcarbamate 

Relevant articles and documents

Use of the Claisen/metathesis reaction sequence for the synthesis of enantiomerically pure 1-aminocycloalkene-1-carboxylic acids

An effective method for the preparation of enantiomerically pure 1-aminocycloalkene-1-carboxylic acids is reported using a chelate Claisen rearrangement-metathesis sequence. Enantioselectivity is achieved through substrate control and a highly ordered transition state, without the use of a chiral auxiliary. A synthesis of 1-aminocyclopent-3-ene-1-carboxylic acid 1 in five steps and 47% overall yield is also described.

Administration of negamycin or deoxynegamycin for the treatment of bacterial infections

The invention provides a method for treating bacterial infections. In one aspect, the invention comprises orally administering a pharmaceutical composition to an animal, wherein the composition comprises a pharmaceutically acceptable excipient and an antibacterial effective amount of negamycin, or a pharmaceutically acceptable salt, prodrug or isomer thereof. An aspect of the invention also relates to a method of treating a bacterial infection, wherein the method comprises intravenously administering a pharmaceutical composition to an animal, and wherein the composition comprises a pharmaceutically acceptable excipient and an antibacterial effective amount of deoxynegamycin, or a pharmaceutically acceptable salt, prodrug or isomer thereof. An aspect of the invention also relates to a method of treating a bacterial infection, wherein the method comprises administering to an animal an antibacterial effective amount of negamycin or deoxynegamycin, or a pharmaceutically acceptable salt, prodrug or isomer thereof, and wherein the infecting bacteria are selected from a group of bacteria consisting of the following: Acinetobacter baumanii, Citrobacter freundii, Enterobacter aerogenes, haemophilus influenzae, Moraxella catarrhalis, Staphylococcus aureus MRSA, Staphylococcus aureus GISA, Staphylococcus epidermis, Streptococcus pneumoniae PenR, Streptococcus pneumoniae PenS and Streptococcus pyogenes.

Cross-metathesis of unsaturated α-amino acid derivatives

Cross-metathesis of homoallylglycine derivatives with aryl- and alkyl-substituted alkenes using the ruthenium catalyst (Cy3P)2Cl2Ru=CHPh 1 has been achieved in 43-55 and 55-66% yield respectively. Allylglycine, vinylglycine and dehydroalanine derivatives have also been examined. Whilst cross-metathesis of allylglycine derivatives with alkyl-substituted alkenes using catalyst 1 may be regarded as a synthetically useful procedure, cross-metathesis reactions of vinylglycine and dehydroalanine derivatives using catalyst 1 are non-viable. Attachment of FmocHagOH 13 to a capped Wang resin, cross-metathesis with dodec-1-ene, and product removal from the resin gives the cross-metathesis product in 74% yield based on FmocHagOH.