(5S,8S)-8-[N-(benzyloxycarbonyl)amino]-6-azabicyclo[10.4.0]hexadeca-1⁽¹²⁾,13,15-triene-2,10-diyne-5-carboxylic acid N-methyl amide

Base Information

• Chemical Name: (5S,8S)-8-[N-(benzyloxycarbonyl)amino]-6-azabicyclo[10.4.0]hexadeca-1⁽¹²⁾,13,15-triene-2,10-diyne-5-carboxylic acid N-methyl amide
• CAS No.: 869115-88-8
• Molecular Formula: C₂₅H₂₃N₃O₄
• Molecular Weight: 429.475

Synonyms:(5S,8S)-8-[N-(benzyloxycarbonyl)amino]-6-azabicyclo[10.4.0]hexadeca-1⁽¹²⁾,13,15-triene-2,10-diyne-5-carboxylic acid N-methyl amide

Chemical Property of (5S,8S)-8-[N-(benzyloxycarbonyl)amino]-6-azabicyclo[10.4.0]hexadeca-1⁽¹²⁾,13,15-triene-2,10-diyne-5-carboxylic acid N-methyl amide

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Technology Process of (5S,8S)-8-[N-(benzyloxycarbonyl)amino]-6-azabicyclo[10.4.0]hexadeca-1⁽¹²⁾,13,15-triene-2,10-diyne-5-carboxylic acid N-methyl amide

There total 6 articles about (5S,8S)-8-[N-(benzyloxycarbonyl)amino]-6-azabicyclo[10.4.0]hexadeca-1⁽¹²⁾,13,15-triene-2,10-diyne-5-carboxylic acid N-methyl amide 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: 37.0%

(S)-5-[2-((S)-4-Amino-4-methylcarbamoyl-but-1-ynyl)-phenyl]-2-benzyloxycarbonylamino-pent-4-ynoic acid methyl ester → (5S,8S)-8-[N-(benzyloxycarbonyl)amino]-6-azabicyclo[10.4.0]hexadeca-1(12),13,15-triene-2,10-diyne-5-carboxylic acid N-methyl amide (869115-88-8)

Guidance literature:

With trimethylaluminum; In hexane; dichloromethane; for 24h; Heating;

DOI:10.1016/j.bmc.2005.07.016

Reference yield:

(1-methylcarbamoyl-but-3-ynyl)-carbamic acid tert-butyl ester → (5S,8S)-8-[N-(benzyloxycarbonyl)amino]-6-azabicyclo[10.4.0]hexadeca-1(12),13,15-triene-2,10-diyne-5-carboxylic acid N-methyl amide (869115-88-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / aq. ammonia; CuI / Pd(PPh₃)2Cl₂ / 1,2-dimethoxy-ethane / 20 °C

2: thionyl chloride / 0 - 20 °C

3: 37 percent / trimethylaluminium / CH₂Cl₂; hexane / 24 h / Heating

With ammonium hydroxide; copper(l) iodide; thionyl chloride; trimethylaluminum; bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; hexane; dichloromethane; 1: Sonogashira coupling;

DOI:10.1016/j.bmc.2005.07.016

Reference yield:

Cbz-L-propargylglycine-OH (869116-13-2) → (5S,8S)-8-[N-(benzyloxycarbonyl)amino]-6-azabicyclo[10.4.0]hexadeca-1(12),13,15-triene-2,10-diyne-5-carboxylic acid N-methyl amide (869115-88-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 55 percent / aq. ammonia; CuI / Pd(PPh₃)2Cl₂ / tetrahydrofuran / 20 °C

2: 69 percent / aq. ammonia; CuI / Pd(PPh₃)2Cl₂ / 1,2-dimethoxy-ethane / 20 °C

3: thionyl chloride / 0 - 20 °C

4: 37 percent / trimethylaluminium / CH₂Cl₂; hexane / 24 h / Heating

With ammonium hydroxide; copper(l) iodide; thionyl chloride; trimethylaluminum; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; 1: Sonogashira coupling / 2: Sonogashira coupling;

DOI:10.1016/j.bmc.2005.07.016

upstream raw materials:

Cbz-L-propargylglycine-OH

(S)-2-(benzyloxycarbonylamino)-5-(2-iodophenyl)pent-4-ynoic acid

(S,S)-2-(benzyloxycarbonylamino)-5-[2-(4-tert-butoxycarbonylamino-4-(methylcarbamoyl)but-1-ynyl)phenyl]pent-4-ynoic acid

1,2-Diiodobenzene

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