N-((2R,3S)-2-(((S)-2-benzamido-N-(4-bromobenzyl)-3-phenylpropanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-yl)biphenyl-4-carboxamide

Base Information

• Chemical Name: N-((2R,3S)-2-(((S)-2-benzamido-N-(4-bromobenzyl)-3-phenylpropanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-yl)biphenyl-4-carboxamide
• CAS No.: 1592908-81-0
• Molecular Formula: C₄₉H₄₆BrN₃O₇
• Molecular Weight: 868.824

Synonyms:N-((2R,3S)-2-(((S)-2-benzamido-N-(4-bromobenzyl)-3-phenylpropanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-yl)biphenyl-4-carboxamide

Chemical Property of N-((2R,3S)-2-(((S)-2-benzamido-N-(4-bromobenzyl)-3-phenylpropanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-yl)biphenyl-4-carboxamide

Chemical Property:

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Technology Process of N-((2R,3S)-2-(((S)-2-benzamido-N-(4-bromobenzyl)-3-phenylpropanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-yl)biphenyl-4-carboxamide

There total 8 articles about N-((2R,3S)-2-(((S)-2-benzamido-N-(4-bromobenzyl)-3-phenylpropanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-yl)biphenyl-4-carboxamide 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: 85.0%

N-((S)-1-((((2R,3S)-3-amino-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-2-yl)methyl)(4-bromobenzyl)amino)-1-oxo-3-phenylpropan-2-yl)benzamide (1592908-75-2) + 4-biphenyl-carboxylic acid chloride (14002-51-8) → N-((2R,3S)-2-(((S)-2-benzamido-N-(4-bromobenzyl)-3-phenylpropanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-yl)biphenyl-4-carboxamide (1592908-81-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/ejoc.201301769

Reference yield:

allyl (2S,3S)-2-(hydroxymethyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate → N-((2R,3S)-2-(((S)-2-benzamido-N-(4-bromobenzyl)-3-phenylpropanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-yl)biphenyl-4-carboxamide (1592908-81-0)

Guidance literature:

Multi-step reaction with 6 steps

1: triphenylphosphine; diethylazodicarboxylate; diphenylphosphoranyl azide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

2: triphenylphosphine / tetrahydrofuran; water / 12 h / 20 °C / Inert atmosphere

3: sodium cyanoborohydride; acetic acid / ethanol / 4 h / 20 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine; PyBroP / dichloromethane / 20 °C / Inert atmosphere

5: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane / 1 h / 0 °C / Inert atmosphere; Darkness

6: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diphenylphosphoranyl azide; sodium cyanoborohydride; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; PyBroP; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1002/ejoc.201301769

Reference yield:

allyl (2R,3S)-2-(azidomethyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate → N-((2R,3S)-2-(((S)-2-benzamido-N-(4-bromobenzyl)-3-phenylpropanamido)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-yl)biphenyl-4-carboxamide (1592908-81-0)

Guidance literature:

Multi-step reaction with 5 steps

1: triphenylphosphine / tetrahydrofuran; water / 12 h / 20 °C / Inert atmosphere

2: sodium cyanoborohydride; acetic acid / ethanol / 4 h / 20 °C / Inert atmosphere

3: N-ethyl-N,N-diisopropylamine; PyBroP / dichloromethane / 20 °C / Inert atmosphere

4: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane / 1 h / 0 °C / Inert atmosphere; Darkness

5: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium cyanoborohydride; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; PyBroP; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1002/ejoc.201301769

upstream raw materials:

N-((S)-1-((((2R,3S)-3-amino-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-2-yl)methyl)(4-bromobenzyl)amino)-1-oxo-3-phenylpropan-2-yl)benzamide

4-biphenyl-carboxylic acid chloride

(2S,3S)-ethyl-3-(allyloxycarbonylamino)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-2-carboxylate

allyl (2R,3S)-2-((4-bromobenzylamino)methyl)-6-((2-methoxyethoxy)methoxy)-2,3-dihydrobenzofuran-3-ylcarbamate

Downstream raw materials:

(7S,10aR,15bS,E)-6-benzoyl-7-benzyl-1-(biphenylcarbonyl)-9-(4-bromobenzyl)-13-((2-methoxyethoxy)methoxy)-1,2,6,7,9,10,10a,15boctahydrobenzofuro[2,3-f][1,4,8]triazacyclododecin-8(5H)-one

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