p-nitrobenzyl (RS)-7--3-methyl-3-cephem-4-carboxylate

Base Information

• Chemical Name: p-nitrobenzyl (RS)-7--3-methyl-3-cephem-4-carboxylate
• CAS No.: 95834-69-8
• Molecular Formula: C₃₀H₂₉ClN₄O₈S₂
• Molecular Weight: 673.167

Synonyms:p-nitrobenzyl (RS)-7--3-methyl-3-cephem-4-carboxylate

Chemical Property of p-nitrobenzyl (RS)-7--3-methyl-3-cephem-4-carboxylate

Chemical Property:

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Technology Process of p-nitrobenzyl (RS)-7--3-methyl-3-cephem-4-carboxylate

There total 7 articles about p-nitrobenzyl (RS)-7--3-methyl-3-cephem-4-carboxylate 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: 87.0%

p-nitrobenzyl ester of 7-aminodeacetoxycephalosporanic acid (29124-83-2) + N-(tert-butoxycarbonyl)(5-chloro-3-benzothienyl)glycine (95835-02-2) → p-nitrobenzyl (RS)-7--3-methyl-3-cephem-4-carboxylate (95834-69-8)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In acetonitrile; for 16h; 1.) 0 deg C, 1 h, 2.) 25 deg C, 4 h;

DOI:10.1021/jm00150a022

Reference yield:

2-(5-chlorobenzo[b]thiophen-3-yl)acetonitrile (23799-60-2) → p-nitrobenzyl (RS)-7--3-methyl-3-cephem-4-carboxylate (95834-69-8)

Guidance literature:

Multi-step reaction with 7 steps

1: aq. HCO₂H

2: HCl / ethanol

3: n-butyl nitrite, sodium methoxide

4: Zn, HCO₂H / methanol / 12 h / 0 °C

5: 1 N NaOH / ethanol / 2 h

6: ethanol; tetrahydrofuran / 12 h

7: 87 percent / EEDQ / acetonitrile / 16 h / 1.) 0 deg C, 1 h, 2.) 25 deg C, 4 h

With hydrogenchloride; sodium hydroxide; formic acid; n-Butyl nitrite; sodium methylate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; zinc; In tetrahydrofuran; methanol; ethanol; acetonitrile;

DOI:10.1021/jm00150a022

Reference yield:

5-chlorobenzothiophene-3-acetic acid (17266-30-7) → p-nitrobenzyl (RS)-7--3-methyl-3-cephem-4-carboxylate (95834-69-8)

Guidance literature:

Multi-step reaction with 6 steps

1: HCl / ethanol

2: n-butyl nitrite, sodium methoxide

3: Zn, HCO₂H / methanol / 12 h / 0 °C

4: 1 N NaOH / ethanol / 2 h

5: ethanol; tetrahydrofuran / 12 h

6: 87 percent / EEDQ / acetonitrile / 16 h / 1.) 0 deg C, 1 h, 2.) 25 deg C, 4 h

With hydrogenchloride; sodium hydroxide; formic acid; n-Butyl nitrite; sodium methylate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; zinc; In tetrahydrofuran; methanol; ethanol; acetonitrile;

DOI:10.1021/jm00150a022

upstream raw materials:

p-nitrobenzyl ester of 7-aminodeacetoxycephalosporanic acid

N-(tert-butoxycarbonyl)(5-chloro-3-benzothienyl)glycine

2-(5-chlorobenzo[b]thiophen-3-yl)acetonitrile

5-chlorobenzothiophene-3-acetic acid

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