(S)-(-)-methyl 2-[bis(tert-butoxycarbonyl)amino]-4-iodobutanoate

Base Information

• Chemical Name: (S)-(-)-methyl 2-[bis(tert-butoxycarbonyl)amino]-4-iodobutanoate
• CAS No.: 224192-25-0
• Molecular Formula: C₁₅H₂₆INO₆
• Molecular Weight: 443.279
• Mol file: 224192-25-0.mol

Synonyms:

Chemical Property of (S)-(-)-methyl 2-[bis(tert-butoxycarbonyl)amino]-4-iodobutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(-)-methyl 2-[bis(tert-butoxycarbonyl)amino]-4-iodobutanoate

There total 6 articles about (S)-(-)-methyl 2-[bis(tert-butoxycarbonyl)amino]-4-iodobutanoate 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: 53.0%

methyl (2S)-2-[bis(tert-butoxycarbonyl)amino]-4-methylsulfonyloxybutanoate (748150-90-5) → (S)-(-)-methyl 2-[bis(tert-butoxycarbonyl)amino]-4-iodobutanoate (224192-25-0) + methyl (2S)-2-(tert-butoxycarbonyl)amino-4-iodobutanoate (101650-14-0)

Guidance literature:

With sodium iodide; In acetone; Reflux;

DOI:10.1055/s-0040-1706144

Reference yield:

methyl (2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]carbonylamino}-4-oxobutanoate (219617-09-1) → (S)-(-)-methyl 2-[bis(tert-butoxycarbonyl)amino]-4-iodobutanoate (224192-25-0) + methyl (2S)-2-(tert-butoxycarbonyl)amino-4-iodobutanoate (101650-14-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

3: sodium iodide / acetone / Reflux

With sodium tetrahydroborate; triethylamine; sodium iodide; In methanol; dichloromethane; acetone;

DOI:10.1055/s-0040-1706144

Reference yield:

methyl (2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]carbonylamino}-4-hydroxybutanoate (224192-24-9) → (S)-(-)-methyl 2-[bis(tert-butoxycarbonyl)amino]-4-iodobutanoate (224192-25-0) + methyl (2S)-2-(tert-butoxycarbonyl)amino-4-iodobutanoate (101650-14-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

2: sodium iodide / acetone / Reflux

With triethylamine; sodium iodide; In dichloromethane; acetone;

DOI:10.1055/s-0040-1706144

upstream raw materials:

methyl (2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]carbonylamino}-4-oxobutanoate

methyl (2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]carbonylamino}-4-hydroxybutanoate

methyl (2S)-2-[bis(tert-butoxycarbonyl)amino]-4-methylsulfonyloxybutanoate

di-tert-butyl dicarbonate

Downstream raw materials:

N₂-(tert-butoxycarbonyl)-L-ornithine

Boc-Arg(Boc)2OH

Refernces