N^α-4-toluenesulfonyl-N^α-methylalanine

Base Information

• Chemical Name: N^α-4-toluenesulfonyl-N^α-methylalanine
• CAS No.: 79821-69-5
• Molecular Formula: C₁₁H₁₅NO₄S
• Molecular Weight: 257.31
• Mol file: 79821-69-5.mol

Synonyms:N^α-4-toluenesulfonyl-N^α-methylalanine

Chemical Property of N^α-4-toluenesulfonyl-N^α-methylalanine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N^α-4-toluenesulfonyl-N^α-methylalanine

There total 5 articles about N^α-4-toluenesulfonyl-N^α-methylalanine 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: 87.0%

(S)-2-[Methyl-(toluene-4-sulfonyl)-amino]-propionic acid isopropyl ester (60522-13-6) → Nα-4-toluenesulfonyl-Nα-methylalanine (79821-69-5)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; for 2h; Heating;

Reference yield:

p-tosyl-L-alanine (4816-81-3,21957-58-4,85471-45-0) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → Nα-4-toluenesulfonyl-Nα-methylalanine (79821-69-5)

Guidance literature:

p-tosyl-L-alanine; formaldehyd; With toluene-4-sulfonic acid; In toluene; for 1h; Reflux; Inert atmosphere; Dean-Stark;

With triethylsilane; trifluoroacetic acid; In chloroform; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c01301

Reference yield:

(S)-2-(Toluene-4-sulfonylamino)-propionic acid isopropyl ester (60522-12-5) → Nα-4-toluenesulfonyl-Nα-methylalanine (79821-69-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NaOH / H₂O / 4 h / Ambient temperature; detergent

2: 87 percent / HCl / H₂O; dioxane / 2 h / Heating

With hydrogenchloride; sodium hydroxide; In 1,4-dioxane; water;

upstream raw materials:

(S)-2-[Methyl-(toluene-4-sulfonyl)-amino]-propionic acid isopropyl ester

(S)-2-(Toluene-4-sulfonylamino)-propionic acid isopropyl ester

p-toluenesulfonyl chloride

p-tosyl-L-alanine

Downstream raw materials:

N-methylalanine

toluene-4-sulfonic acid

Refernces

• 1、 Hlavacek, Jan,Fric, Ivo,Budesinsky, Milos,Blaha, Karel. "AN ALTERNATIVE ROUTE TO Nα-METHYLAMINO ACID DERIVATIVES: SYNTHESIS AND CONFORMATION OF SOME Nα-acetyl-Nα-METHYLAMINO ACID METHYLAMIDES". . p. 2473 - 2494. Retrieved 2007/10/02.