N-(4-Methylbenzene-1-sulfonyl)-L-leucyl chloride

Base Information

• Chemical Name: N-(4-Methylbenzene-1-sulfonyl)-L-leucyl chloride
• CAS No.: 61341-05-7
• Molecular Formula: C13H18ClNO3S
• Molecular Weight: 303.81
• DSSTox Substance ID: DTXSID70513117
• Wikidata: Q82372728
• Mol file: 61341-05-7.mol

Synonyms:61341-05-7;N-(4-Methylbenzene-1-sulfonyl)-L-leucyl chloride;DTXSID70513117

Chemical Property of N-(4-Methylbenzene-1-sulfonyl)-L-leucyl chloride

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 303.0695923
• Heavy Atom Count: 19
• Complexity: 395

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(CC(C)C)C(=O)Cl
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N[C@@H](CC(C)C)C(=O)Cl

Technology Process of N-(4-Methylbenzene-1-sulfonyl)-L-leucyl chloride

There total 7 articles about N-(4-Methylbenzene-1-sulfonyl)-L-leucyl chloride 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:

(S)-4-methyl-2-(toluene-4-sulfonamido)pentanoic acid (1220-80-0,67368-40-5,150614-61-2) → N-tosylleucine acid chloride (61341-05-7)

Guidance literature:

With diethyl ether; phosphorus pentachloride;

DOI:10.1021/ja01569a071

Reference yield:

(R)-4-methyl-2-(4-methylphenylsulfonamido)pentanoic acid (150614-61-2) → Tosyl-L-leucin-chlorid (61341-05-7)

Guidance literature:

With thionyl chloride; In benzene; at 60 ℃; for 3h;

DOI:10.1021/jo034275j

Reference yield:

L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) → N-tosylleucine acid chloride (61341-05-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / NaOH / H₂O / 6 h / 60 °C

2: thionyl chloride / benzene / 3 h / 60 °C

With sodium hydroxide; thionyl chloride; In water; benzene;

DOI:10.1021/jo034275j

upstream raw materials:

(R)-4-methyl-2-(4-methylphenylsulfonamido)pentanoic acid

(R)-leucine

p-toluenesulfonyl chloride

(S)-4-methyl-2-(toluene-4-sulfonamido)pentanoic acid

Downstream raw materials:

(S)-1-[(S)-4-methyl-2-tosylaminopentanoyl]-6-(1-methyl-1H-indol-3-yl)-3-phenyl-1,6-dihydro-1,2,4-triazin-5(4H)-one

(S)-1-[(S)-4-methyl-2-tosylaminopentanoyl]-6-(2-methyl-1H-indol-3-yl)-3-phenyl-1,6-dihydro-1,2,4-triazin-5(4H)-one

(S)-2-[(S)-4-methyl-2-tosylaminopentanoyl]-3-(1H-indol-3-yl)-6-phenyl-3,4-dihydro-1,2,4-triazin-5(2H)-one

(S)-1-[(S)-4-methyl-2-tosylaminopentanoyl]-6-(1H-indol-3-yl)-3-phenyl-1,6-dihydro-1,2,4-triazin-5(4H)-one

Refernces

• 1、 Kanyiva, Kyalo Stephen,Horiuchi, Masashi,Shibata, Takanori. "Metal-Free N–H/C–H Coupling for Efficient Asymmetric Synthesis of Chiral Dihydroquinoxalinones from Readily Available α-Amino Acids". supporting information. p. 1067 - 1070. Retrieved 2018/03/06.
• 2、 Aguilar-Castro, Liliana,Tlahuextl, Margarita,Tapia-Benavides, Antonio R.,Tlahuext, Hugo. "Synthesis and structural studies of new N-(p-toluenesulfonyl)amino acid o-phenolamides". . p. 247 - 253. Retrieved 2007/10/03.