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

Base Information

Chemical Name:(S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-((trimethylsilyl)ethynyl)benzoate
CAS No.:1597416-58-4
Molecular Formula:C₂₁H₃₀N₂O₅Si
Molecular Weight:418.565
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 3 articles about (S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-((trimethylsilyl)ethynyl)benzoate 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%

: 1597416-57-3
(S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-iodobenzoate

: 1066-54-2
trimethylsilylacetylene

: 1597416-58-4
(S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-((trimethylsilyl)ethynyl)benzoate

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 60 ℃; for 16h; Inert atmosphere;
DOI:10.1002/anie.201309353

Reference yield:

: 283173-76-2
methyl 3-amino-2-iodobenzoate

: 1597416-58-4
(S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-((trimethylsilyl)ethynyl)benzoate

Guidance literature:: Multi-step reaction with 2 steps

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

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

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; 2: |Sonogashira Cross-Coupling;
DOI:10.1002/anie.201309353

Reference yield:

: 93415-79-3
methyl 2-iodo-3-nitrobenzoate

: 1597416-58-4
(S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-((trimethylsilyl)ethynyl)benzoate

Guidance literature:: Multi-step reaction with 3 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

With iron(III) chloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 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