methyl (2S)-2-{N-[3-(2-iodophenyl)prop-2-yn-1-yl](4-methylbenzene)sulfonamido}-3-methylbutanoate

Base Information

• Chemical Name: methyl (2S)-2-{N-[3-(2-iodophenyl)prop-2-yn-1-yl](4-methylbenzene)sulfonamido}-3-methylbutanoate
• CAS No.: 1362825-41-9
• Molecular Formula: C₂₂H₂₄INO₄S
• Molecular Weight: 525.407
• Mol file: 1362825-41-9.mol

Synonyms:methyl (2S)-2-{N-[3-(2-iodophenyl)prop-2-yn-1-yl](4-methylbenzene)sulfonamido}-3-methylbutanoate

Chemical Property of methyl (2S)-2-{N-[3-(2-iodophenyl)prop-2-yn-1-yl](4-methylbenzene)sulfonamido}-3-methylbutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S)-2-{N-[3-(2-iodophenyl)prop-2-yn-1-yl](4-methylbenzene)sulfonamido}-3-methylbutanoate

There total 1 articles about methyl (2S)-2-{N-[3-(2-iodophenyl)prop-2-yn-1-yl](4-methylbenzene)sulfonamido}-3-methylbutanoate 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: 82.0%

1-iodo-2-(3-iodoprop-1-ynyl)benzene (1253043-95-6) + Methyl (S)-N-<(4-methylphenyl)sulfonyl>valinate (51220-85-0,21957-66-4) → methyl (2S)-2-{N-[3-(2-iodophenyl)prop-2-yn-1-yl](4-methylbenzene)sulfonamido}-3-methylbutanoate (1362825-41-9)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo202580y

Reference yield: 85.0%

methyl (2S)-2-{N-[3-(2-iodophenyl)prop-2-yn-1-yl](4-methylbenzene)sulfonamido}-3-methylbutanoate (1362825-41-9) + propargyl alcohol (107-19-7) → methyl (2S)-2-(N-{3-[2-(3-hydroxyprop-1-yn-1-yl)phenyl]prop-2-yn-1-yl}(4-methylbenzene)sulfonamido)-3-methylbutanoate (1362825-44-2)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; triethylamine; In tetrahydrofuran; at 40 ℃; for 4.75h; Inert atmosphere;

DOI:10.1021/jo202580y

Reference yield:

methyl (2S)-2-{N-[3-(2-iodophenyl)prop-2-yn-1-yl](4-methylbenzene)sulfonamido}-3-methylbutanoate (1362825-41-9) → methyl (2S)-3-methyl-2-{N-[(3-{[(4-methylbenzene)sulfonyl]-methyl}naphthalen-2-yl)methyl](4-methylbenzene)-sulfonamido}but-3-enoate (1362826-23-0)

Guidance literature:

Multi-step reaction with 5 steps

1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; triethylamine / tetrahydrofuran / 4.75 h / 40 °C / Inert atmosphere

2: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.67 h / 0 °C / Inert atmosphere

5: mesoporous silica grafted with a tertiary amino group (GA-SBA-15) / acetonitrile / 18 h / 80 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jo202580y

upstream raw materials:

1-iodo-2-(3-iodoprop-1-ynyl)benzene

Methyl (S)-N-<(4-methylphenyl)sulfonyl>valinate

Downstream raw materials:

methyl (2S)-3-methyl-2-{N-[(3-{[(4-methylbenzene)sulfonyl]-methyl}naphthalen-2-yl)methyl](4-methylbenzene)-sulfonamido}but-3-enoate

methyl 3-methyl-2-{N-[(3-{[(4-methylbenzene)sulfonyl]methyl}naphthalen-2-yl)methyl](4-methylbenzene)sulfonamido}but-2-enoate

methyl (2S)-3-methyl-2-{N-[3-(2-{3-[(4-methylphenyl)sulfanyl]prop-1-yn-1-yl}phenyl)prop-2-yn-1-yl](4-methylbenzene)sulfonamido}butanoate

methyl (2S)-3-methyl-2-{N-[3-(2-{3-[(4-methylbenzene)sulfonyl]prop-1-yn-1-yl}phenyl)prop-2-yn-1-yl](4-methylbenzene)sulfonamido}butanoate