N-[6-(N-chlorambucilamino)hexanoyl]-DL-o-tyrosinol

Base Information

• Chemical Name: N-[6-(N-chlorambucilamino)hexanoyl]-DL-o-tyrosinol
• CAS No.: 1263819-77-7
• Molecular Formula: C₂₉H₄₁Cl₂N₃O₄
• Molecular Weight: 566.568
• Mol file: 1263819-77-7.mol

Synonyms:

Chemical Property of N-[6-(N-chlorambucilamino)hexanoyl]-DL-o-tyrosinol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[6-(N-chlorambucilamino)hexanoyl]-DL-o-tyrosinol

There total 4 articles about N-[6-(N-chlorambucilamino)hexanoyl]-DL-o-tyrosinol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-hydroxy-phenylalanine (709-16-0,2370-61-8,7423-92-9,24008-77-3) → N-[6-(N-chlorambucilamino)hexanoyl]-DL-o-tyrosinol (1263819-77-7)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuryl dichloride / 12 h / 0 °C / Reflux

2: benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 24 h / 20 °C

3: lithium borohydride / diethyl ether; dichloromethane / 3 h / Inert atmosphere; Cooling with ice

With lithium borohydride; sulfuryl dichloride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1007/s00726-011-1152-3

Reference yield:

6-aminohexanoic acid (60-32-2,93208-38-9) → N-[6-(N-chlorambucilamino)hexanoyl]-DL-o-tyrosinol (1263819-77-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sulfuric acid; 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 0.5 h / Inert atmosphere; Reflux

1.2: 12 h / 20 °C / Inert atmosphere

1.3: 5 h / 0 - 20 °C

2.1: benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 24 h / 20 °C

3.1: lithium borohydride / diethyl ether; dichloromethane / 3 h / Inert atmosphere; Cooling with ice

With lithium borohydride; sulfuric acid; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1007/s00726-011-1152-3

Reference yield:

6-(N-chlorambucilamino)hexanoic acid (1260612-36-9) + methyl 2-amino-3-(2-hydroxyphenyl)propanoate (Hydrochloride) (194795-20-5) → N-[6-(N-chlorambucilamino)hexanoyl]-DL-o-tyrosinol (1263819-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 24 h / 20 °C

2: lithium borohydride / diethyl ether; dichloromethane / 3 h / Inert atmosphere; Cooling with ice

With lithium borohydride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1007/s00726-011-1152-3

upstream raw materials:

6-(N-chlorambucilamino)hexanoic acid

methyl 2-amino-3-(2-hydroxyphenyl)propanoate (Hydrochloride)

2-hydroxy-phenylalanine

6-aminohexanoic acid

Refernces

• 1、 -. "ANTICANCER AGENTS BASED ON AMINO ACID DERIVATIVES". Page/Page column 52-53. . Retrieved 2011/02/24.