2212-76-2

Basic information

• Product Name: Z-LYS(BOC)-OH DCHA
• Synonyms: N-EPSILON-BOC-N-ALPHA-Z-L-LYSINE DCHA SALT;N-EPSILON-BOC-N-ALPHA-Z-L-LYSINE DICYCLOHEXYLAMINE SALT;N-EPSILON-BUTOXYCARBONYL-N-ALPHA-Z-L-LYSINE DCHA SALT;N-ALPHA-BENZYLOXYCARBONYL-N-EPSILON-TERT-BUTYLOXYCARBONYL-L-LYSINE DICYCLOHEXYLAMINE;N-ALPHA-CARBOBENZOXY-N-EPSILON-T-BUTOXYCARBONYL-L-LYSINE DICYCLOHEXYLAMMONIUM SALT;N-ALPHA-Z-N-EPSILON-BOC-L-LYSINE DICYCLOHEXYLAMINE SALT;Z-N-EPSILON-BOC-L-LYSINE DICYCLOHEXYLAMMONIUM SALT;Z-L-LYS(BOC)-OH DCHA
• CAS NO: 2212-76-2
• Molecular Formula: C₁₂H₂₃N*C₁₉H₂₈N₂O₆
• Molecular Weight: 561.75
• EINECS: 218-663-1
• Product Categories: Z-Amino Acids and Derivatives
• Mol File: 2212-76-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 154-156 °C
• Boiling Point: 587 °C at 760 mmHg
• Flash Point: 308.8 °C
• Appearance: white crystals
• Vapor Pressure: 1.26E-14mmHg at 25°C
• Storage Temp.: 2-8°C
• BRN: 4650895
• CAS DataBase Reference: Z-LYS(BOC)-OH DCHA(CAS DataBase Reference)
• NIST Chemistry Reference: Z-LYS(BOC)-OH DCHA(2212-76-2)
• EPA Substance Registry System: Z-LYS(BOC)-OH DCHA(2212-76-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2212-76-2(Hazardous Substances Data)

Usage

Description

Z-LYS(BOC)-OH DCHA, also known as N-benzyloxycarbonyl-L-lysine dicyclohexylammonium hydroxide, is a chemical compound that serves as an intermediate in the synthesis of various pharmaceuticals. It is characterized by its white crystalline appearance and plays a crucial role in the development of potential neuroprotective agents.

Uses

Used in Pharmaceutical Industry:
Z-LYS(BOC)-OH DCHA is used as a pharmaceutical intermediate for the preparation of dimeric dipeptide nerve growth factor mimetics. These mimetics have the potential to act as neuroprotective agents, offering therapeutic benefits in the treatment of neurological disorders and conditions.
As a key component in the synthesis of nerve growth factor mimetics, Z-LYS(BOC)-OH DCHA contributes to the development of novel therapeutic strategies for neurodegenerative diseases, such as Alzheimer's, Parkinson's, and multiple sclerosis. Its role in the pharmaceutical industry highlights its importance in advancing the field of neuroprotection and promoting overall brain health.

InChI:InChI=1/C19H28N2O6.C12H23N/c1-19(2,3)27-17(24)20-12-8-7-11-15(16(22)23)21-18(25)26-13-14-9-5-4-6-10-14;1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h4-6,9-10,15H,7-8,11-13H2,1-3H3,(H,20,24)(H,21,25)(H,22,23);11-13H,1-10H2/t15-;/m0./s1

Synthetic route

benzyl-8-quinolyl carbonate (19506-72-0) + di-tert-butyl dicarbonate (24424-99-5) + L-Lysine hydrochloride (657-27-2, 10098-89-2) + N-cyclohexyl-cyclohexanamine (101-83-7) → Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2)

Conditions	Yield
Multistep reaction;	91%

Z-Lys(Boc)-OH (2389-60-8) + N-cyclohexyl-cyclohexanamine (101-83-7) → Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2)

Conditions	Yield
In Isopropyl acetate

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → Z-Lys(-Boc)-Osu (3338-34-9)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 0℃;	98%
Stage #1: Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt With sulfuric acid In ethyl acetate for 0.5h; Stage #2: 1-hydroxy-pyrrolidine-2,5-dione With dicyclohexyl-carbodiimide In ethyl acetate at 20℃; for 20h;	95%

glycine ethyl ester hydrochloride (5680-79-5) + Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → Nα-Benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysylglycine Methyl Ester (10342-52-6)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 25℃;	90%

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) + N-acetyl-p-phenylenediamine (122-80-5) → N2-(benzyloxycarbonyl)-N6-(tert-butoxycarbonyl)-L-lysin-4-acetamidoanilide (139009-82-8)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide 1) 0-5 deg C, 1 h, 2) room temperature, 4 h;	72%

diazomethane (186581-53-3, 908094-01-9) + Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → Nα-(benzyloxycarbonyl)-Nε-(tert-butoxycarbonyl)-L-lysine methyl ester (2389-49-3)

Conditions	Yield
(i) ion-exchange resin + form>, EtOH, (ii) /BRN= 102415/, Et2O; Multistep reaction;

L-alanine methyl ester hydrochloride (2491-20-5) + Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → Cbz-Lys(Boc)-Ala-OMe (50466-60-9)

Conditions	Yield
With 4-methyl-morpholine; chloroformic acid ethyl ester 1.) THF, -15 deg C, 2.) H2O, THF, -15 deg to r.t., 45 h; Yield given. Multistep reaction;

Coumarin 151 (53518-15-3) + Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → 7-(Nα-Z-Nε-Boc-L-Lysinamido)-4-(trifluoromethyl)-coumarin (73496-37-4)

Conditions	Yield
With 4-methyl-morpholine; toluene-4-sulfonic acid; isobutyl chloroformate Yield given. Multistep reaction;

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) + 1-pentanamine (110-58-7) → N2-(benzyloxycarbonyl)-N6-<(tert-butoxy)carbonyl>-N1-pentyllysinamid (159360-26-6)

Conditions	Yield
Yield given. Multistep reaction;

bis(p-nitrophenyl)sulfite (25887-81-4) + Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → N2-benzyloxycarbonyl-N6-t-butoxycarbonyl-L-lysine 4-nitrophenyl ester (2212-69-3)

Conditions	Yield
(i) aq. citric acid, Et2O, (ii) /BRN= 1893948/, Py; Multistep reaction;

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) + 4-tert-butyl 1-methyl L-aspartate hydrochloride (2673-19-0) → (S)-2-((S)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-hexanoylamino)-succinic acid 4-tert-butyl ester 1-methyl ester

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → ((S)-5-Amino-5-pentylcarbamoyl-pentyl)-carbamic acid tert-butyl ester

Conditions	Yield
Multi-step reaction with 2 steps 2: hydrogen / 5percent Pd/C / methanol / 3 h View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → N2-<3-<(3-aminopropyl)amino>propanoyl>-N1-pentyllysinamid-trihydrochlorid

Conditions	Yield
Multi-step reaction with 4 steps 2: hydrogen / 5percent Pd/C / methanol / 3 h 3: 1.) CDI / 1.) THF, 3 h, room temp., 2.) THF, 12 h 4: 84 percent / HCl sol. / dioxane / 4 h View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → N6-<(tert-butoxy)carbonyl>-N2-<3--N-<3-<(tert-butoxy)carbonylamino>propyl>amino>propanoyl>-N'-pentyllysinamid (159360-35-7)

Conditions	Yield
Multi-step reaction with 3 steps 2: hydrogen / 5percent Pd/C / methanol / 3 h 3: 1.) CDI / 1.) THF, 3 h, room temp., 2.) THF, 12 h View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → N2-<3-<(3-aminopropyl)amino>propanoyl>-N1-pentyllysinamid-tris(trifluoroacetat)

Conditions	Yield
Multi-step reaction with 4 steps 2: hydrogen / 5percent Pd/C / methanol / 3 h 3: 1.) CDI / 1.) THF, 3 h, room temp., 2.) THF, 12 h 4: 78 percent / CH2Cl2 / 0.5 h View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → N2-(benzyloxycarbonyl)-L-lysin-4-acetamidoanilide 4-toluenesulfonate (139010-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / 4-(dimethylamino)pyridine, 1-ethyl-<3-(dimethylamino)propyl>carbodiimide hydrochloride / CH2Cl2; dimethylformamide / 1) 0-5 deg C, 1 h, 2) room temperature, 4 h 2: 82 percent / H2 / 10percent Pd-C / acetic acid / 1 h / 25 °C / 2068.6 Torr View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → Z-Lys(Boc)-Ala-OCH2CH=CH2 (136497-31-9, 136497-45-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) ClCO2Et, N-methylmorpholine, 2.) N-methylmorpholine / 1.) THF, -15 deg C, 2.) H2O, THF, -15 deg to r.t., 45 h 2: 93 percent / LiBr, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / 22 h / 0 °C View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → N-(Nα-carbobenzoxy-Nε-tert-butoxycarbonyl-L-lysyl)glycine (47689-13-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / N-hydroxybenzotriazole, dicyclohexylcarbodiimide / dimethylformamide / 0 - 25 °C 2: LiOH / methanol View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → Nα-Benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysylglycyl-L-asparaginyl-L-leucine Methyl Ester (87136-45-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / N-hydroxybenzotriazole, dicyclohexylcarbodiimide / dimethylformamide / 0 - 25 °C 2: LiOH / methanol 3: 24 percent / N-hydroxybenzotriazole, dicyclohexylcarbodiimide / dimethylformamide / Ambient temperature View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → Nα-Benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysylglycyl-L-asparaginyl-L-leucine Lithium Salt (87136-46-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / N-hydroxybenzotriazole, dicyclohexylcarbodiimide / dimethylformamide / 0 - 25 °C 2: LiOH / methanol 3: 24 percent / N-hydroxybenzotriazole, dicyclohexylcarbodiimide / dimethylformamide / Ambient temperature 4: LiOH / 2-methyl-propan-2-ol; H2O View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → (S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate (3017-32-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) ion-exchange resin + form>, EtOH, (ii) /BRN= 102415/, Et2O 2: H2, AcOH / Pd / methanol View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → C54H104N6O4*2ClH

Conditions

Yield

Multi-step reaction with 5 steps 1: potassium hydrogensulfate / ethyl acetate / 0.25 h 2: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / ethyl acetate; water 3: palladium on activated charcoal; hydrogen / N,N-dimethyl-formamide 4: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide 5: hydrogenchloride / ethyl acetate; chloroform / 0.75 h View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → bis-(Nε-t-butyloxycarbonyl-lysyl) hexamethylenediamide

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydrogensulfate / ethyl acetate / 0.25 h 2: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / ethyl acetate; water 3: palladium on activated charcoal; hydrogen / N,N-dimethyl-formamide View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → C64H120N6O8 (609819-75-2)

Conditions

Yield

Multi-step reaction with 4 steps 1: potassium hydrogensulfate / ethyl acetate / 0.25 h 2: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / ethyl acetate; water 3: palladium on activated charcoal; hydrogen / N,N-dimethyl-formamide 4: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → bis-(N-benzyloxycarbonyl-Nε-t-butyloxycaxbonyl-lysyl)hexamethylenediamide

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydrogensulfate / ethyl acetate / 0.25 h 2: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / ethyl acetate; water View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → C50H96N6O4*2ClH

Conditions

Yield

Multi-step reaction with 5 steps 1: potassium hydrogensulfate / ethyl acetate / 0.25 h 2: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / ethyl acetate; water 3: palladium on activated charcoal; hydrogen / N,N-dimethyl-formamide 4: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide 5: hydrogenchloride / ethyl acetate; chloroform / 0.75 h View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → C51H98N6O4*2ClH

Conditions

Yield

Multi-step reaction with 5 steps 1: potassium hydrogensulfate / ethyl acetate / 0.25 h 2: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / ethyl acetate; water 3: palladium on activated charcoal; hydrogen / N,N-dimethyl-formamide 4: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide 5: hydrogenchloride / ethyl acetate; chloroform / 0.75 h View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → C52H100N6O4*2ClH

Conditions

Yield

Multi-step reaction with 5 steps 1: potassium hydrogensulfate / ethyl acetate / 0.25 h 2: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / ethyl acetate; water 3: palladium on activated charcoal; hydrogen / N,N-dimethyl-formamide 4: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide 5: hydrogenchloride / ethyl acetate; chloroform / 0.75 h View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → C53H102N6O4*2ClH

Conditions

Yield

Multi-step reaction with 5 steps 1: potassium hydrogensulfate / ethyl acetate / 0.25 h 2: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / ethyl acetate; water 3: palladium on activated charcoal; hydrogen / N,N-dimethyl-formamide 4: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide 5: hydrogenchloride / ethyl acetate; chloroform / 0.75 h View Scheme

Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt (2212-76-2) → C55H106N6O4*2ClH

Conditions

Yield

Multi-step reaction with 5 steps 1: potassium hydrogensulfate / ethyl acetate / 0.25 h 2: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / ethyl acetate; water 3: palladium on activated charcoal; hydrogen / N,N-dimethyl-formamide 4: 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide 5: hydrogenchloride / ethyl acetate; chloroform / 0.75 h View Scheme

Upstream product

• 19506-72-0 benzyl-8-quinolyl carbonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 657-27-2 L-Lysine hydrochloride 
• 101-83-7 N-cyclohexyl-cyclohexanamine 
• 2389-60-8 Z-Lys(Boc)-OH 

Downstream Products

• 2212-69-3 N₂-benzyloxycarbonyl-N₆-t-butoxycarbonyl-L-lysine 4-nitrophenyl ester 
• 3338-34-9 Z-Lys(-Boc)-Osu 
• 2389-60-8 Z-Lys(Boc)-OH 
• 3017-32-1 (S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate 
• 87136-46-7 N^α-Benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-L-lysylglycyl-L-asparaginyl-L-leucine Lithium Salt 
• 87136-45-6 N^α-Benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-L-lysylglycyl-L-asparaginyl-L-leucine Methyl Ester 
• 47689-13-4 N-(N^α-carbobenzoxy-N^ε-tert-butoxycarbonyl-L-lysyl)glycine 
• 136497-31-9 Z-Lys(Boc)-Ala-OCH₂CH=CH₂ 
• 139010-01-8 N²-(benzyloxycarbonyl)-L-lysin-4-acetamidoanilide 4-toluenesulfonate 
• 139009-82-8 N²-(benzyloxycarbonyl)-N⁶-(tert-butoxycarbonyl)-L-lysin-4-acetamidoanilide 
• 159360-26-6 N²-(benzyloxycarbonyl)-N⁶-<(tert-butoxy)carbonyl>-N¹-pentyllysinamid 
• 73496-37-4 7-(N^α-Z-N^ε-Boc-L-Lysinamido)-4-(trifluoromethyl)-coumarin 
• 50466-60-9 Cbz-Lys(Boc)-Ala-OMe 
• 10342-52-6 N^α-Benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-L-lysylglycine Methyl Ester 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF ε-ALKOXYCARBONYLLYSINES AND THEIR ANALOGUES

A process for the preparation of ω-alkoxycarbonylamino-α-aminoacids and α,ω orthogonally diprotected diaminoacids from α,ω-diaminoacids using 1- alkoxycarbonylbenzotriazoles as protecting agents is disclosed. In an alternative embodiment, carbamoylating agents in the presence of benzotriazoles are used instead of 1-alkoxycarbonylbenzotriazoles. This reaction is preferably applied to the preparation of ε- alkoxycarbonyllysines from lysine. A process for the preparation of t-butoxycarbonylbenzotriazoles and novel complexes of ω-alkoxycarbonylamino-α-aminoacids with benzotriazoles are also disclosed.