5959-35-3

Usage

InChI:InChI=1/C4H9NO2.ClH/c5-3-1-2-4(6)7;/h1-3,5H2,(H,6,7);1H

Upstream product

• 70288-77-6 4-(Methoxycarbonylamino)buttersaeure-methylester 
• 7647-01-0 hydrogenchloride 
• 57294-38-9 N-(tert-butoxycarbonyl)-4-aminobutanoic acid 
• 56-12-2 4-amino-n-butyric acid 
• 81292-85-5 C₈H₁₂N₂O₆P₂^(4-)*4Na⁽¹⁺⁾ 

Downstream Products

• 554412-80-5 5-(benzyloxycarbonyl-methyl-amino)-2-(3-carboxy-propylamino)-4-oxo-5,6-dihydro-4H-pyrimidine-1-carboxylic acid tert-butyl ester 
• 13031-60-2 methyl γ-aminobutyrate hydrochloride 
• 137048-10-3 4-amino butyric acid chloride hydrochloride 

Relevant academic research and scientific papers

An Efficient Route to N-Monosubstituted Guanidino-Lactams

A small library of guanidino-lactams were synthesized in four steps and good overall yields by following the routes: preparation of guanylating agents, synthesis of protected guanidino-acids, cyclization to fully protected guanidino-lactams, and deprotection to the target compounds. The guanidino-lactams were assayed as antimicrobials on E. coli showing no significant antibiotic activity.

Thermodynamics of protonation of amino acid carboxylate groups from 50 to 125°C

Flow calorimetry has been used to study the interaction of glycine, DL-α-alanine, DL-2-aminobutyric acid, β-alanine, 4-aminobutyric acid, and 6-aminocaproic acid with protons in aqueous solutions from 323.15 K to 398.15 K and at 1.52 MPa. LogK, ΔH°, ΔS°, and ΔC°p for the protonation of the carboxylate groups of these amino acids have been obtained at each temperature studied. Equations are given expressing these values as functions of temperature. The protonation reactions are exothermic at lower temperatures and become endothermic as temperature increases. The logK, ΔH°, and ΔS° values are close together over the temperature range studied for the protonation of α-amino acids, i.e., glycine, DL-α-a/anine, and 2-aminobutyric acid. At each temperature, the magnitudes of these thermodynamic quantities increase as the number of methylene groups between the amino group and the carboxylate group increases. The ΔC°p value for the protonation of the carboxyl group is found to lie between those of an isocoulombic reaction and a charge reduction reaction. At 323.15 K, the protonation reactions of the carboxylate groups have larger ΔC°p values which approach those associated with charge reduction reactions. As the temperature increases, ΔC°p decreases and approaches those found for isocoulombic reactions. This result is explained by considering long-range and short-range solvent effects. The trend in ΔH° and ΔS° with temperature and with charge separation in the zwitterions is interpreted in terms of solvent-solute interactions and the electrostatic interaction of the two oppositely charged groups within the molecule.

Salts of 4-aminobutyric acid and 6-aminohexanoic acid behaving as molecular Velcro

The crystal structures of eight novel carboxyalkylammonium salts, (+H3N(CH2)nCOOH)X-, are reported, with n = 4 and X = Cl, Br and I in structures 1, 2 and 3, respectively, and n = 6 and X = Cl, Br·0.5H2O, Cl·0.5H2O, NO3 and ClO4 in structures 4, 5, 6, 7 and 8. The members of this family of compounds were found to display significant structural diversity, and a careful analysis of the structures employing the principles of crystal engineering was done to explain the observed trends and differences, specifically also the interdigitation or non-interdigitation of alkyl chains. It was found that a primary hydrogen bonding network formed between the ammonium groups and halide or oxo-anions, which plays a major structure-directing role. The structures may be likened to molecular Velcro, in which secondary hydrogen bonding interactions involving the carboxylic acid groups act as "hooks" to link primary networks.

Transkarbams as transdermal permeation enhancers: Effects of ester position and ammonium carbamate formation

Transkarbam 12, an ammonium carbamate formed by the reaction of dodecyl 6-aminohexanoate with carbon dioxide, is a highly active, broad-spectrum, nontoxic, and nonirritant transdermal permeation enhancer. It probably acts by a dual mechanism: a part of its activity is associated with the carbamic acid salt and/or its decomposition in the acidic stratum corneum. The ammonium ester thereby released is an active enhancer species as well, and its activity highly depends on the position of the ester group.

Geminal Diphosphonic Acids Containing Amidino Groups

The reaction of amides or nitriles with H3PO4/PCl3 leads in some cases to the formation of amidinoalkylidenediphophonic acids.In the case of formamide under specified conditions, amidinomethylenediphosphonic acid (4) is formed, with succin- or glutaramides (or with the nitriles) the heterocyclic, geminal diphosphonic acids 10 are obtained.By the reaction of 2-pyrrolidinone 12 with PCl3/H2O in addition to the expected 2,2-pyrrolidinylidenediphosphonic acid (11a) an amidine is isolated, for which the structure 15 is suggested.The alkaline hydrolyses of these compounds and the corresponding reaction products are described.

Aminosaeuren, I. Darstellung von Aminosaeuren aus Halogencarbonsaeure-alkylestern mit Alkalimetallcyanaten

α- and ω-halo- as well as α,ω-dihalocarboxylic alkyl esters react with potassium cyanate in the presence of alcohol at 80 - 120 deg C in dipolar aprotic solvents to yield α- and ω-(alkoxycarbonylamino)- and α,ω-bis(alkoxycarbonylamino)carboxylic alkyl esters, respectively, in good yields.Hydrolytic cleavage of these mono- or diurethanes with an aqueous solution of hydrochloric acid/formic acid leads to the corresponding amino acid hydrochlorides in nearly quantitative yields.