N-(p-toluenesulfonyl)-N-(tert-butoxycarbonyl)-methallylamine

Base Information

• Chemical Name: N-(p-toluenesulfonyl)-N-(tert-butoxycarbonyl)-methallylamine
• CAS No.: 529409-31-2
• Molecular Formula: C₁₆H₂₃NO₄S
• Molecular Weight: 325.429
• Mol file: 529409-31-2.mol

Synonyms:N-(p-toluenesulfonyl)-N-(tert-butoxycarbonyl)-methallylamine

Chemical Property of N-(p-toluenesulfonyl)-N-(tert-butoxycarbonyl)-methallylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(p-toluenesulfonyl)-N-(tert-butoxycarbonyl)-methallylamine

There total 4 articles about N-(p-toluenesulfonyl)-N-(tert-butoxycarbonyl)-methallylamine 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: 91.0%

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide (18303-04-3) + 3-hydroxy-2-methyl-1-propene (513-42-8) → N-(p-toluenesulfonyl)-N-(tert-butoxycarbonyl)-methallylamine (529409-31-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 0.166667h;

DOI:10.3762/bjoc.14.250

Reference yield: 61.0%

2-methyl-3-bromo-1-propene (1458-98-6) + N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide (18303-04-3) → N-(p-toluenesulfonyl)-N-(tert-butoxycarbonyl)-methallylamine (529409-31-2)

Guidance literature:

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃;

2-methyl-3-bromo-1-propene; In N,N-dimethyl-formamide; mineral oil; at 20 ℃;

DOI:10.1021/acs.orglett.6b02706

Reference yield:

toluene-4-sulfonamide (70-55-3) → N-(p-toluenesulfonyl)-N-(tert-butoxycarbonyl)-methallylamine (529409-31-2)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; dmap / 1,2-dichloro-ethane / 20 °C

2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.17 h / 20 °C

With dmap; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dichloro-ethane; 2: |Mitsunobu Displacement;

DOI:10.3762/bjoc.14.250

upstream raw materials:

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide

3-hydroxy-2-methyl-1-propene

2-methyl-3-bromo-1-propene

toluene-4-sulfonamide

Downstream raw materials:

4-methyl-N-(2-methylallyl)-N-(prop-2-ynyl)benzenesulfonamide

N-(4-hydroxy-but-2-ynyl)-4-methyl-N-(2-methylallyl)-benzenesulfonamide

N-(2-methylallyl)-4-toluenesulfonamide

C₂₂H₂₃NO₄S