3844-53-9

Basic information

• Product Name: Ethyl 2,6-diaminohexanoate dihydrochloride
• Synonyms: LYSINE-OET 2 HCL;L-LYSINE ETHYL ESTER DIHYDROCHLORIDE;H-LYS-OET 2HCL;ethyl L-lysinate dihydrochloride;L-Lysine Ethyl Ester 2HCl;L-LYSIN-ETHYLESTER-DIHYDROCHLORID;L-Lysine ethyl ester dihy;L-Lysine ethyl·dihydrochloride
• CAS NO: 3844-53-9
• Molecular Formula: C₈H₁₈N₂O₂*2ClH
• Molecular Weight: 247.16
• EINECS: 223-340-3
• Product Categories: Lysine [Lys, K];Amino Acids and Derivatives;Amino hydrochloride;Amino Acid Derivatives;Amino Acids;I - ZPeptide Synthesis;Lysine;Modified Amino Acids;Peptide Synthesis
• Mol File: 3844-53-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: ~150 °C (dec.)
• Boiling Point: 261.9 °C at 760 mmHg
• Flash Point: 97.3 °C
• Appearance: White Powder
• Density: g/cm³
• Vapor Pressure: 0.0112mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: Aqueous Acid (Slightly, Heated), Water (Sparingly)
• Sensitive: Hygroscopic
• BRN: 3697099
• CAS DataBase Reference: Ethyl 2,6-diaminohexanoate dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2,6-diaminohexanoate dihydrochloride(3844-53-9)
• EPA Substance Registry System: Ethyl 2,6-diaminohexanoate dihydrochloride(3844-53-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3
• Hazardous Substances Data: 3844-53-9(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

L-?Lysine Ethyl Ester Dihydrochloride is a reagent used in the preparation of myxochelin which has been shown to possess strong anti-tumor activity.

InChI:InChI=1/C8H18N2O2/c1-2-12-8(11)7(10)5-3-4-6-9/h7H,2-6,9-10H2,1H3/p+2/t7-/m0/s1

Synthetic route

ethanol (64-17-5) + L-Lysine hydrochloride (657-27-2, 10098-89-2) → L-lysine ethyl ester dihydrochloride (3844-53-9)

Conditions	Yield
With thionyl chloride Reflux;	87%
With thionyl chloride at -10℃; for 6h; Reflux;	87%
With hydrogenchloride at 70℃; for 5h;

ethanol (64-17-5) + L-lysine-dihydrochloride → L-lysine ethyl ester dihydrochloride (3844-53-9)

Conditions	Yield
With hydrogenchloride

C11H15N2O5PolS + L-lysine ethyl ester dihydrochloride (3844-53-9) → C22H38N4O6Pol2S2

Conditions	Yield
Stage #1: C11H15N2O5PolS With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h; Stage #2: L-lysine ethyl ester dihydrochloride With dmap In dichloromethane at 20℃; for 42h;	94%

L-lysine ethyl ester dihydrochloride (3844-53-9) + trityl chloride (76-83-5) → ethyl 2-amino-6-(tritylamino)hexanoate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 6h;	88.8%

2,3-dimethoxybenzoic acid (1521-38-6) + L-lysine ethyl ester dihydrochloride (3844-53-9) → ethyl N2,N6-bis(2,3-dimethoxybenzoyl)-L-lysinate

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	85%

L-lysine ethyl ester dihydrochloride (3844-53-9) + trimellitic Anhydride (552-30-7) → C26H22N2O10 (1281900-48-8)

Conditions	Yield
With pyridine; acetic acid at 20℃; for 6h; Reflux;	79%
With pyridine; acetic acid for 8h; Reflux;

2-(2-methoxyethoxy)acetic acid (16024-56-9) + L-lysine ethyl ester dihydrochloride (3844-53-9) → di-(2-methoxyethoxyacetyl)-L-lysine ethyl ester

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Cooling with ice;	77.8%

L-lysine ethyl ester dihydrochloride (3844-53-9) + geldanmycin (30562-34-6) → (S)-ethyl 2-amino-6-(((4E,6Z,8S,9S,10E,12S,13R,14S,16R)-9-(carbamoyloxy)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-19-yl)amino)hexanoate

Conditions	Yield
With triethylamine In tetrahydrofuran; methanol at 60℃;	74.1%

L-lysine ethyl ester dihydrochloride (3844-53-9) + 2-methyl-5-nitroimidazole-1-acetic acid (1010-93-1) → ethyl 2,6-bis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetamido)hexanoate

Conditions	Yield
Stage #1: 2-methyl-5-nitroimidazole-1-acetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 0.25h; Inert atmosphere; Stage #2: L-lysine ethyl ester dihydrochloride With triethylamine In N,N-dimethyl-formamide Inert atmosphere;	69%

C29H51NO15 + L-lysine ethyl ester dihydrochloride (3844-53-9) → C52H102N2O26 (870821-07-1)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	66%

formaldehyd (50-00-0) + 2-sulfanylidene-6-(trifluoromethyl)-2,3-dihydropyrimidin-4(1H)-one (368-54-7) + L-lysine ethyl ester dihydrochloride (3844-53-9) → ethyl (2S)-2,6-bis(6-oxo-8-(trifluoromethyl)-3,4-dihydro-2,6-pyrimido[2,1-b][1,3,5]thiadiazin-3(2H,3H,4H,6H)-yl)hexanoate

Conditions	Yield
In water; acetonitrile at 20℃;	51%
In water; acetonitrile at 20℃; Mannich Aminomethylation; regiospecific reaction;	51%

[(2R,3R,4R)-3,4-diacetoxy-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl acetate (82913-19-7) + L-lysine ethyl ester dihydrochloride (3844-53-9) → 4-[((1S)-1-amino-1-ethoxycarbonyl)pentyl]amino-1-(β-D-2,3,5-tri-O-acetylribofuranosyl)pyrimidine-2(1H)-one

Conditions	Yield
With triethylamine In acetonitrile	42.3%

L-lysine ethyl ester dihydrochloride (3844-53-9) + 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-(1,2,4-triazol-1-yl)pyrimidin-2(1H)-one (136112-90-8) → 4-[((1S)-1-amino-1-ethoxycarbonyl)pentyl]amino-1-(β-D-2,3,5-tri-O-benzoylribofuranosyl)pyrimidine-2(1H)-one

Conditions	Yield
With triethylamine In acetonitrile	40.8%

formaldehyd (50-00-0) + m-xylylene diisocyanide (188540-42-3) + Boc-Glu(OBzl)-OH (13574-13-5) + L-lysine ethyl ester dihydrochloride (3844-53-9) → C54H72N6O14 (1034473-44-3)

Conditions	Yield
Stage #1: formaldehyd; L-lysine ethyl ester dihydrochloride In methanol at 20℃; for 2h; Ugi type macrocyclization; Stage #2: Boc-Glu(OBzl)-OH In methanol for 0.5h; Ugi type macrocyclization; Stage #3: m-xylylene diisocyanide In methanol Ugi type macrocyclization;	40%

L-lysine ethyl ester dihydrochloride (3844-53-9) + 3-formylrifamycin SV (13292-22-3) → C46H65N3O14

Conditions	Yield
Stage #1: 3-formylrifamycin SV With hydrogenchloride In ethanol; dichloromethane Stage #2: L-lysine ethyl ester dihydrochloride With potassium hydroxide In methanol; ethanol; dichloromethane at 40℃; for 0.5h; Stage #3: With sodium cyanoborohydride In methanol; ethanol; dichloromethane at 20℃; for 1h;	33%

2-fluoro-1-methoxy-4-nitrobenzene (455-93-6) + L-lysine ethyl ester dihydrochloride (3844-53-9) → 5-nitroguaiacol (636-93-1) + 2-(2-methoxy-5-nitrophenyl)amino-ε-caprolactame (124431-94-3)

Conditions	Yield
In acetonitrile for 4h; Ambient temperature; Irradiation; pH=10;	A 22% B 6%

L-lysine ethyl ester dihydrochloride (3844-53-9) + copper(II) o-hydroxybenzoate (3890-90-2) → Nα,Nε-disalicylidene-L-lysine ethyl ester; copper (II)-salt

Conditions	Yield
With ethanol; sodium acetate

10-undecenoic acid (112-38-9) + L-lysine ethyl ester dihydrochloride (3844-53-9) → N,N'-Bis-(10-undecenoyl)-L-lysinethylester (61796-85-8)

Conditions	Yield
(i) ClCO2Et, Et3N, (ii) /BRN= 3697099/; Multistep reaction;
(i) Et3N, DMF, (ii) ClCO2Et, (iii) /BRN= 3697099/; Multistep reaction;

tert-Butyl 4-nitrophenyl carbonate (13303-10-1) + L-lysine ethyl ester dihydrochloride (3844-53-9) → Nα,Nε-Di-tert.-butyloxycarbonyl-L-lysin-ethylester (99872-16-9)

Conditions	Yield
With pyridine

L-lysine ethyl ester dihydrochloride (3844-53-9) + n-decanoyl chloride (112-13-0) → N,N'-Bis-(decanoyl)-L-lysinethylester (61796-82-5)

Conditions	Yield
With triethylamine
With triethylamine In N,N-dimethyl-formamide

L-lysine ethyl ester dihydrochloride (3844-53-9) → lysine tetrapeptide (997-20-6) + poly(L-lysine), 5-mer (19431-21-1) + L-lysine (56-87-1) + dilysine (13184-13-9) + Lys-Lys-Lys (13184-14-0) + hexalysine (554-38-1)

Conditions	Yield
multistep reaction; 1.) trypsin, Na2CO3 buffer pH 10.0, 25 deg C, 2.) NaOH, 60 deg C, 15 min; trypsin-catalyzed oligomerization of L-lysine esters, pH-dependence, reaction rate, kinetics, effect of NaCl; other L-lysin alkyl esters, enzyme or amino acids;

L-lysine ethyl ester dihydrochloride (3844-53-9) → lysine tetrapeptide (997-20-6) + poly(L-lysine), 5-mer (19431-21-1) + Lys-Lys-Lys (13184-14-0) + lysine peptide K8 (21743-34-0)

Conditions	Yield
With sodium hydroxide 1.) trypsin, sodium carbonate buffer pH 10.0, 25 deg C, 1 h, 2.) 60 deg C, 15 min; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

L-lysine ethyl ester dihydrochloride (3844-53-9) → lysine tetrapeptide (997-20-6) + poly(L-lysine), 5-mer (19431-21-1) + Lys-Lys-Lys (13184-14-0) + hexalysine (554-38-1)

Conditions	Yield
With sodium hydroxide 1.) trypsin, sodium carbonate buffer pH 10.0, 25 deg C, 1 h, 2.) 60 deg C, 15 min; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

L-lysine ethyl ester dihydrochloride (3844-53-9) → lysine tetrapeptide (997-20-6) + poly(L-lysine), 5-mer (19431-21-1) + Lys-Lys-Lys (13184-14-0) + (Lys)7 (7532-36-7)

Conditions	Yield
With sodium hydroxide 1.) trypsin, sodium carbonate buffer pH 10.0, 25 deg C, 1 h, 2.) 60 deg C, 15 min; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

L-lysine ethyl ester dihydrochloride (3844-53-9) → lysine tetrapeptide (997-20-6) + L-lysine (56-87-1) + dilysine (13184-13-9) + Lys-Lys-Lys (13184-14-0)

Conditions	Yield
With sodium hydroxide 1.) trypsin, sodium carbonate buffer pH 10.0, 25 deg C, 3 h, 2.) 60 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given;

L-lysine ethyl ester dihydrochloride (3844-53-9) → L-lysine (56-87-1) + dilysine (13184-13-9) + Lys-Lys-Lys (13184-14-0)

Conditions	Yield
With sodium hydroxide 1.) trypsin, sodium carbonate buffer pH 10.0, 25 deg C, 24 h, 2.) 60 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given;

L-lysine ethyl ester dihydrochloride (3844-53-9) + benzyl chloroformate (501-53-1) → Nα,Nξ-di-Cbz-L-lysine ethyl ester (83173-67-5)

Conditions	Yield
With potassium carbonate In water for 20h;	14.00 g

L-lysine ethyl ester dihydrochloride (3844-53-9) → Nα,Nε-bis(benzyloxycarbonyl)-D-lysinal (138207-66-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 14.00 g / K2CO3 / H2O / 20 h 2: 89 percent / CaCl2, NaBH4 / tetrahydrofuran; ethanol / 20 h / 0 - 20 °C 3: 1.) DMSO, COCl2, 2.) Et3N / 1.) CH2Cl2, -63 deg C, 20 min, 2.) CH2Cl2, -63 deg C, 20 min View Scheme

L-lysine ethyl ester dihydrochloride (3844-53-9) → N,N-bis-Cbz-L-lysinol (137649-64-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 14.00 g / K2CO3 / H2O / 20 h 2: 89 percent / CaCl2, NaBH4 / tetrahydrofuran; ethanol / 20 h / 0 - 20 °C View Scheme

L-lysine ethyl ester dihydrochloride (3844-53-9) → (1R,2R,3S)-1-cyclohexyl-3,7-bisheptane-1,2-diol

Conditions	Yield
Multi-step reaction with 4 steps 1: 14.00 g / K2CO3 / H2O / 20 h 2: 89 percent / CaCl2, NaBH4 / tetrahydrofuran; ethanol / 20 h / 0 - 20 °C 3: 1.) DMSO, COCl2, 2.) Et3N / 1.) CH2Cl2, -63 deg C, 20 min, 2.) CH2Cl2, -63 deg C, 20 min View Scheme

Upstream product

• 64-17-5 ethanol 
• 657-27-2 L-Lysine hydrochloride 

Downstream Products

• 83173-67-5 N_α,N_ξ-di-Cbz-L-lysine ethyl ester 
• 120243-02-9 myxochelin A 
• 1034473-44-3 C₅₄H₇₂N₆O₁₄ 
• 2483-46-7 Boc-Lys(Boc)-OH 
• 137649-64-0 N,N-bis-Cbz-L-lysinol 
• 138207-66-6 N^α,N^ε-bis(benzyloxycarbonyl)-D-lysinal 
• 56-87-1 L-lysine 
• 13184-13-9 dilysine 
• 13184-14-0 Lys-Lys-Lys 
• 997-20-6 lysine tetrapeptide 
• 19431-21-1 poly(L-lysine), 5-mer 
• 7532-36-7 (Lys)7 
• 554-38-1 hexalysine 
• 21743-34-0 lysine peptide K₈ 

Relevant articles and documents

Interfacial synthesis and properties of l-lysine-derived optically active poly(ester-imide)s

l-Lysine hydrochloride was transformed to ethyl l-lysine dihydrochloride. This salt was reacted with trimellitic anhydride to yield the corresponding diacid (1). Interfacial polycondensation results novel poly(ester-imide)s (PEIa-i). These polymers have inherent viscosities in the range of 0.23-0.47 dl g-1, display optical activity, and are readily soluble in polar aprotic solvents. They start to decompose (T10%) above 350 °C and display glass-transition temperatures at 100.42-172.81 °C. All of the above polymers were fully characterized by UV, FT-IR and 1H NMR spectroscopy, elemental analysis, TGA, DSC, inherent viscosity measurement and specific rotation.

Synthesis and antimicrobial characterization of novel l-lysine gemini surfactants pended with reactive groups

A series of novel quaternary ammonium gemini surfactants of l-lysine containing ester group were synthesized with high yield rate. The antibacterial and antifungal activities of these gemini surfactants were evaluated by quantifying the minimal inhibitory concentration (MIC). The results indicated that the quaternary ammonium gemini surfactants exhibited improved activity against a broad spectrum of Gram-positive and Gram-negative bacteria as well as fungi. The pended ester group provides a reactive site for incorporating the surfactant into polymers, thus leading to the polymers with high antimicrobial efficiency.