N-[(1R,2R,6S)-4-bromo-2-(1-ethylpropoxy)-6-azidocyclohex-3-en-1-yl]acetamide

Base Information

• Chemical Name: N-[(1R,2R,6S)-4-bromo-2-(1-ethylpropoxy)-6-azidocyclohex-3-en-1-yl]acetamide
• CAS No.: 1062100-81-5
• Molecular Formula: C₁₃H₂₁BrN₄O₂
• Molecular Weight: 345.239

Synonyms:N-[(1R,2R,6S)-4-bromo-2-(1-ethylpropoxy)-6-azidocyclohex-3-en-1-yl]acetamide

Chemical Property of N-[(1R,2R,6S)-4-bromo-2-(1-ethylpropoxy)-6-azidocyclohex-3-en-1-yl]acetamide

Chemical Property:

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Technology Process of N-[(1R,2R,6S)-4-bromo-2-(1-ethylpropoxy)-6-azidocyclohex-3-en-1-yl]acetamide

There total 1 articles about N-[(1R,2R,6S)-4-bromo-2-(1-ethylpropoxy)-6-azidocyclohex-3-en-1-yl]acetamide 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: 84.0%

N-[(1R,2R,6R)-4-bromo-2-(1-ethylpropoxy)-6-hydroxycyclohex-3-en-1-yl]acetamide (1122581-40-1) → N-[(1R,6R)-4-bromo-6-(1-ethylpropoxy)cyclohex-2,4-dien-1-yl]acetamide (1122581-41-2) + N-[(1R,2R,6S)-4-bromo-2-(1-ethylpropoxy)-6-azidocyclohex-3-en-1-yl]acetamide (1062100-81-5)

Guidance literature:

With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine; In tetrahydrofuran; at 40 ℃; for 24h;

DOI:10.1002/anie.200801959

Reference yield: 83.0%

N-[(1R,2R,6S)-4-bromo-2-(1-ethylpropoxy)-6-azidocyclohex-3-en-1-yl]acetamide (1062100-81-5) + phosphonic acid diethyl ester (762-04-9) → diethyl (3R,4R,5S)-4-acetamido-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 90 ℃; for 12h;

DOI:10.1002/anie.200801959

Reference yield: 81.0%

ethanol (64-17-5) + N-[(1R,2R,6S)-4-bromo-2-(1-ethylpropoxy)-6-azidocyclohex-3-en-1-yl]acetamide (1062100-81-5) + bis(triphenylphosphine)dicarbonylnickel(0) → oseltamivir (204255-06-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 80 ℃; for 24h;

DOI:10.1002/anie.200801959

upstream raw materials:

N-[(1R,2R,6R)-4-bromo-2-(1-ethylpropoxy)-6-hydroxycyclohex-3-en-1-yl]acetamide

Downstream raw materials:

oseltamivir

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