(5R,6R)-3-Benzyl-4-[2-((R)-1-ethoxycarbonyl-ethoxycarbonyl)-eth-(E)-ylidene]-8-methyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (R)-1-ethoxycarbonyl-ethyl ester

Base Information

• Chemical Name: (5R,6R)-3-Benzyl-4-[2-((R)-1-ethoxycarbonyl-ethoxycarbonyl)-eth-(E)-ylidene]-8-methyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (R)-1-ethoxycarbonyl-ethyl ester
• CAS No.: 124562-42-1
• Molecular Formula: C₂₈H₃₆N₂O₉
• Molecular Weight: 544.602

Synonyms:

Chemical Property of (5R,6R)-3-Benzyl-4-[2-((R)-1-ethoxycarbonyl-ethoxycarbonyl)-eth-(E)-ylidene]-8-methyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (R)-1-ethoxycarbonyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (5R,6R)-3-Benzyl-4-[2-((R)-1-ethoxycarbonyl-ethoxycarbonyl)-eth-(E)-ylidene]-8-methyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (R)-1-ethoxycarbonyl-ethyl ester

There total 12 articles about (5R,6R)-3-Benzyl-4-[2-((R)-1-ethoxycarbonyl-ethoxycarbonyl)-eth-(E)-ylidene]-8-methyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (R)-1-ethoxycarbonyl-ethyl ester 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: 26.0%

Acrylate of (S)-ethyl lactate (92173-15-4) + 1-Benzyl-4-methyl-6-oxo-1,4,5,6-tetrahydro-pyrazine-2-carbonitrile (124562-39-6) → (2R,3R,5S)-5-Benzylcarbamoyl-2-[3-((S)-1-ethoxycarbonyl-ethoxycarbonyl)-propionyl]-1-methyl-pyrrolidine-3-carboxylic acid (S)-1-ethoxycarbonyl-ethyl ester (124581-10-8) + (5R,6S)-3-Benzyl-4-[2-((R)-1-ethoxycarbonyl-ethoxycarbonyl)-eth-(E)-ylidene]-8-methyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (R)-1-ethoxycarbonyl-ethyl ester (124562-42-1,124600-96-0,124600-97-1,124600-98-2) + (5R,6R)-3-Benzyl-4-[2-((R)-1-ethoxycarbonyl-ethoxycarbonyl)-eth-(E)-ylidene]-8-methyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (R)-1-ethoxycarbonyl-ethyl ester (124562-42-1,124600-96-0,124600-97-1,124600-98-2)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; Heating;

DOI:10.1021/jo00289a005

Reference yield: 26.0%

Acrylate of (S)-ethyl lactate (92173-15-4) + 1-Benzyl-4-methyl-6-oxo-1,4,5,6-tetrahydro-pyrazine-2-carbonitrile (124562-39-6) → (2R,3R,5S)-5-Benzylcarbamoyl-2-[3-((S)-1-ethoxycarbonyl-ethoxycarbonyl)-propionyl]-1-methyl-pyrrolidine-3-carboxylic acid (S)-1-ethoxycarbonyl-ethyl ester (124581-10-8) + (5R,6S)-3-Benzyl-4-[2-((R)-1-ethoxycarbonyl-ethoxycarbonyl)-eth-(E)-ylidene]-8-methyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (R)-1-ethoxycarbonyl-ethyl ester (124562-42-1,124600-96-0,124600-97-1,124600-98-2) + (5R,6R)-3-Benzyl-4-[2-((R)-1-ethoxycarbonyl-ethoxycarbonyl)-eth-(E)-ylidene]-8-methyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (R)-1-ethoxycarbonyl-ethyl ester (124562-42-1,124600-96-0,124600-97-1,124600-98-2)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; Heating;

DOI:10.1021/jo00289a005

Reference yield:

N-benzyl-2-(methylamino)acetamide (74963-37-4) → (5R,6S)-3-Benzyl-4-[2-((R)-1-ethoxycarbonyl-ethoxycarbonyl)-eth-(E)-ylidene]-8-methyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (R)-1-ethoxycarbonyl-ethyl ester (124562-42-1,124600-96-0,124600-97-1,124600-98-2)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / benzene / 87 h / Heating

2: 63 percent / 6N HCl

3: 72 percent / BF₃*OEt₂ / Ambient temperature

4: 53 percent / m-chloroperbenzoic acid / CH₂Cl₂ / Heating

5: 22 percent / BF₃*OEt₂ / acetonitrile / Heating

With hydrogenchloride; boron trifluoride diethyl etherate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile; benzene;

DOI:10.1021/jo00289a005

upstream raw materials:

Acrylate of (S)-ethyl lactate

1-Benzyl-4-methyl-6-oxo-1,4,5,6-tetrahydro-pyrazine-2-carbonitrile

N-benzyl-2-(methylamino)acetamide

1-Benzyl-6-hydroxy-4-methyl-piperazin-2-one

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