2,2'-(ethyne-1,2-diyl)bis(3-((S)-2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)benzoic acid)

Base Information

• Chemical Name: 2,2'-(ethyne-1,2-diyl)bis(3-((S)-2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)benzoic acid)
• CAS No.: 1597416-72-2
• Molecular Formula: C₅₀H₅₄N₄O₁₄
• Molecular Weight: 934.997
• Mol file: 1597416-72-2.mol

Synonyms:2,2'-(ethyne-1,2-diyl)bis(3-((S)-2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)benzoic acid)

Chemical Property of 2,2'-(ethyne-1,2-diyl)bis(3-((S)-2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)benzoic acid)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2'-(ethyne-1,2-diyl)bis(3-((S)-2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)benzoic acid)

There total 8 articles about 2,2'-(ethyne-1,2-diyl)bis(3-((S)-2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)benzoic acid) 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: 48.0%

(S)-diphenyl 2,2'-(ethyne-1,2-diyl)bis(3-((S)-2-(((benzyloxy)carbonyl)amino)-5-(tertbutoxy)-5-oxopentanamido)benzoate) (1597416-71-1) → 2,2'-(ethyne-1,2-diyl)bis(3-((S)-2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)benzoic acid) (1597416-72-2)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; for 2h; Inert atmosphere;

DOI:10.1002/anie.201309353

Reference yield:

2-iodo-3-nitrobenzoic acid (5398-69-6) → 2,2'-(ethyne-1,2-diyl)bis(3-((S)-2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)benzoic acid) (1597416-72-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

2.2: 2 h / Inert atmosphere

3.1: tin(II) chloride dihdyrate / ethyl acetate / 4 h / Inert atmosphere

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

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

6.1: water; lithium hydroxide / tetrahydrofuran / 2 h / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; oxalyl dichloride; tin(II) chloride dihdyrate; water; sodium hydride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; lithium hydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 5.1: |Sonogashira Cross-Coupling;

DOI:10.1002/anie.201309353

Reference yield:

2-iodo-3-nitrobenzoyl chloride (51640-62-1) → 2,2'-(ethyne-1,2-diyl)bis(3-((S)-2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)benzoic acid) (1597416-72-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

1.2: 2 h / Inert atmosphere

2.1: tin(II) chloride dihdyrate / ethyl acetate / 4 h / Inert atmosphere

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

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

5.1: water; lithium hydroxide / tetrahydrofuran / 2 h / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tin(II) chloride dihdyrate; water; sodium hydride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; dicyclohexyl-carbodiimide; lithium hydroxide; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; 4.1: |Sonogashira Cross-Coupling;

DOI:10.1002/anie.201309353

upstream raw materials:

phenyl 3-amino-2-iodobenzoate

(S)-phenyl 3-(2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)-2-iodobenzoate

(S)-phenyl 3-(2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)-2-ethynylbenzoate

(S)-phenyl 3-(2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)-2-((trimethylsilyl)ethynyl)benzoate

Downstream raw materials:

di-tert-butyl 5,5'-((ethyne-1,2-diylbis(3-(((S)-6-((tert-butoxycarbonyl)amino)-1-(isobutylamino)-1-oxohexan-2-yl)carbamoyl)-2,1-phenylene))bis(azanediyl))(4S,4'S)-bis(4-(((benzyloxy)carbonyl)amino)-5-oxopentanoate)