methyl 4-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]but-2-ynoate

Base Information

• Chemical Name: methyl 4-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]but-2-ynoate
• CAS No.: 819867-59-9
• Molecular Formula: C₂₂H₃₃NO₅SSi
• Molecular Weight: 451.659
• Mol file: 819867-59-9.mol

Synonyms:methyl 4-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]but-2-ynoate

Chemical Property of methyl 4-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]but-2-ynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]but-2-ynoate

There total 3 articles about methyl 4-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]but-2-ynoate 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: 80.0%

methyl chloroformate (79-22-1) + N-((2E)-4-{[tert-butyl(dimethyl)silyl]oxy}but-2-en-1-yl)-4-methyl-N-prop-2-yn-1-ylbenzenesulfonamide (819867-58-8) → methyl 4-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]but-2-ynoate (819867-59-9)

Guidance literature:

N-((2E)-4-{[tert-butyl(dimethyl)silyl]oxy}but-2-en-1-yl)-4-methyl-N-prop-2-yn-1-ylbenzenesulfonamide; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

methyl chloroformate; In tetrahydrofuran; at -78 - 20 ℃; for 1h;

DOI:10.1021/ja046824o

Reference yield:

4-methyl-N-prop-2-ynylbenzenesulfonamide (55022-46-3) → methyl 4-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]but-2-ynoate (819867-59-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 83 percent / (η³-C3H5PdCl)2; Ph3P; Cs2CO3 / tetrahydrofuran / 1 h / 60 °C

2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

2.2: 80 percent / tetrahydrofuran / 1 h / -78 - 20 °C

With n-butyllithium; bis(η3-allyl-μ-chloropalladium(II)); caesium carbonate; triphenylphosphine; In tetrahydrofuran;

DOI:10.1021/ja046824o

Reference yield:

Carbonic acid (Z)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl ester methyl ester (194301-35-4) → methyl 4-[[(E)-4-(tert-butyldimethylsilyloxy)but-2-enyl]-(4-methylbenzenesulfonyl)amino]but-2-ynoate (819867-59-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 83 percent / (η³-C3H5PdCl)2; Ph3P; Cs2CO3 / tetrahydrofuran / 1 h / 60 °C

2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

2.2: 80 percent / tetrahydrofuran / 1 h / -78 - 20 °C

With n-butyllithium; bis(η3-allyl-μ-chloropalladium(II)); caesium carbonate; triphenylphosphine; In tetrahydrofuran;

DOI:10.1021/ja046824o

upstream raw materials:

methyl chloroformate

N-((2E)-4-{[tert-butyl(dimethyl)silyl]oxy}but-2-en-1-yl)-4-methyl-N-prop-2-yn-1-ylbenzenesulfonamide

4-methyl-N-prop-2-ynylbenzenesulfonamide

Carbonic acid (Z)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl ester methyl ester