(S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-ethynylbenzoate

Base Information

• Chemical Name: (S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-ethynylbenzoate
• CAS No.: 1597416-59-5
• Molecular Formula: C₁₈H₂₂N₂O₅
• Molecular Weight: 346.383
• Mol file: 1597416-59-5.mol

Synonyms:(S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-ethynylbenzoate

Chemical Property of (S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-ethynylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-ethynylbenzoate

There total 4 articles about (S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-ethynylbenzoate 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%

(S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-((trimethylsilyl)ethynyl)benzoate (1597416-58-4) → (S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-ethynylbenzoate (1597416-59-5)

Guidance literature:

With methanol; potassium carbonate; for 0.25h; Inert atmosphere;

DOI:10.1002/anie.201309353

Reference yield:

methyl 2-iodo-3-nitrobenzoate (93415-79-3) → (S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-ethynylbenzoate (1597416-59-5)

Guidance literature:

Multi-step reaction with 4 steps

1: acetic acid; iron(III) chloride / 2.5 h / 110 °C / Reflux; Inert atmosphere

2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; dicyclohexyl-carbodiimide / tetrahydrofuran / 16.25 h / -10 - 60 °C / Inert atmosphere

3: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 16 h / 60 °C / Inert atmosphere

4: potassium carbonate; methanol / 0.25 h / Inert atmosphere

With methanol; iron(III) chloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; 3: |Sonogashira Cross-Coupling;

DOI:10.1002/anie.201309353

Reference yield:

(S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-iodobenzoate (1597416-57-3) → (S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-ethynylbenzoate (1597416-59-5)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 16 h / 60 °C / Inert atmosphere

2: potassium carbonate; methanol / 0.25 h / Inert atmosphere

With methanol; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; triethylamine; In N,N-dimethyl-formamide; 1: |Sonogashira Cross-Coupling;

DOI:10.1002/anie.201309353

upstream raw materials:

methyl 3-amino-2-iodobenzoate

methyl 2-iodo-3-nitrobenzoate

(S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-iodobenzoate

(S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-((trimethylsilyl)ethynyl)benzoate

Downstream raw materials:

(S)-dimethyl 2,2'-(ethyne-1,2-diyl)bis(3-((S)-2-((tert-butoxycarbonyl)amino)propanamido)benzoate)

C₃₂H₃₈N₄O₁₀

di-tert-butyl ((2S,2'S)-(((S)-ethyne-1,2-diylbis(3-(((S)-1-(isobutylamino)-1-oxopropan-2-yl)carbamoyl)-2,1-phenylene))bis(azanediyl))bis(1-oxopropane-2,1-diyl))dicarbamate

(S)-2,2'-(ethyne-1,2-diyl)bis(3-((S)-2-acetamidopropanamido)-N-((S)-1-(isobutylamino)-1-oxopropan-2-yl)benzamide)