(6R,7R)-3-{(S)-3-((R)-4-Acetylamino-4-tert-butoxycarbonyl-butyrylamino)-3-[(R)-1-((R)-1-tert-butoxycarbonyl-ethylcarbamoyl)-ethylcarbamoyl]-propyl}-7-amino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: (6R,7R)-3-{(S)-3-((R)-4-Acetylamino-4-tert-butoxycarbonyl-butyrylamino)-3-[(R)-1-((R)-1-tert-butoxycarbonyl-ethylcarbamoyl)-ethylcarbamoyl]-propyl}-7-amino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester
• CAS No.: 651059-41-5
• Molecular Formula: C₄₀H₅₈N₆O₁₂S
• Molecular Weight: 847

Synonyms:(6R,7R)-3-{(S)-3-((R)-4-Acetylamino-4-tert-butoxycarbonyl-butyrylamino)-3-[(R)-1-((R)-1-tert-butoxycarbonyl-ethylcarbamoyl)-ethylcarbamoyl]-propyl}-7-amino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Chemical Property of (6R,7R)-3-{(S)-3-((R)-4-Acetylamino-4-tert-butoxycarbonyl-butyrylamino)-3-[(R)-1-((R)-1-tert-butoxycarbonyl-ethylcarbamoyl)-ethylcarbamoyl]-propyl}-7-amino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

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Technology Process of (6R,7R)-3-{(S)-3-((R)-4-Acetylamino-4-tert-butoxycarbonyl-butyrylamino)-3-[(R)-1-((R)-1-tert-butoxycarbonyl-ethylcarbamoyl)-ethylcarbamoyl]-propyl}-7-amino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

There total 11 articles about (6R,7R)-3-{(S)-3-((R)-4-Acetylamino-4-tert-butoxycarbonyl-butyrylamino)-3-[(R)-1-((R)-1-tert-butoxycarbonyl-ethylcarbamoyl)-ethylcarbamoyl]-propyl}-7-amino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl 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:

3-chloromethyl-7β-tert-butylcarbonylamino-3-cephem-4-carboxylic acid p-methoxybenzyl ester (134866-27-6) → (6R,7R)-3-{(S)-3-((R)-4-Acetylamino-4-tert-butoxycarbonyl-butyrylamino)-3-[(R)-1-((R)-1-tert-butoxycarbonyl-ethylcarbamoyl)-ethylcarbamoyl]-propyl}-7-amino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (651059-41-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 4.5 g / NaI / butan-2-one / 20 °C

2.1: 68 percent / acetonitrile / 20 °C

3.1: potassium trimethylsilanoate / acetonitrile; CHCl₃ / 0.5 h / cooling

3.2: 77 percent / acetonitrile; CHCl₃; CH₂Cl₂ / 3 h / 20 °C

4.1: 54 percent / H₂; acetic acid / Pd/C / methanol / 3 h

5.1: 5.6 g / triethylamine / CH₂Cl₂ / 3 h / -78 - 20 °C

6.1: 46 percent / H₂ / Pd/C / tetrahydrofuran

7.1: Jones reagent / acetone / 2 h / cooling

7.2: HOBt; EDCl / CH₂Cl₂ / 20 °C

7.3: tin(II) chloride; acetyl chloride / dimethylformamide / 1 h / 20 °C

8.1: iodomethylsilane; 2,6-ditert-butyl-4-methylpyridine / acetonitrile / 5 h / cooling

With 2,6-di-tert-butyl-4-methylpyridine; jones reagent; (iodomethyl)silane; potassium trimethylsilonate; hydrogen; acetic acid; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetone; acetonitrile; butanone;

DOI:10.1021/ja038445l

Reference yield:

C16H27NO6 (651059-35-7) → (6R,7R)-3-{(S)-3-((R)-4-Acetylamino-4-tert-butoxycarbonyl-butyrylamino)-3-[(R)-1-((R)-1-tert-butoxycarbonyl-ethylcarbamoyl)-ethylcarbamoyl]-propyl}-7-amino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (651059-41-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 5.6 g / triethylamine / CH₂Cl₂ / 3 h / -78 - 20 °C

2.1: 46 percent / H₂ / Pd/C / tetrahydrofuran

3.1: Jones reagent / acetone / 2 h / cooling

3.2: HOBt; EDCl / CH₂Cl₂ / 20 °C

3.3: tin(II) chloride; acetyl chloride / dimethylformamide / 1 h / 20 °C

4.1: iodomethylsilane; 2,6-ditert-butyl-4-methylpyridine / acetonitrile / 5 h / cooling

With 2,6-di-tert-butyl-4-methylpyridine; jones reagent; (iodomethyl)silane; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetone; acetonitrile;

DOI:10.1021/ja038445l

Reference yield:

4-methoxybenzyl-7-amino-3-chloromethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride (106773-36-8) → (6R,7R)-3-{(S)-3-((R)-4-Acetylamino-4-tert-butoxycarbonyl-butyrylamino)-3-[(R)-1-((R)-1-tert-butoxycarbonyl-ethylcarbamoyl)-ethylcarbamoyl]-propyl}-7-amino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (651059-41-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 51 percent / N-trimethylsilylacetamide / CH₂Cl₂ / 20 °C

2.1: 4.5 g / NaI / butan-2-one / 20 °C

3.1: 68 percent / acetonitrile / 20 °C

4.1: potassium trimethylsilanoate / acetonitrile; CHCl₃ / 0.5 h / cooling

4.2: 77 percent / acetonitrile; CHCl₃; CH₂Cl₂ / 3 h / 20 °C

5.1: 54 percent / H₂; acetic acid / Pd/C / methanol / 3 h

6.1: 5.6 g / triethylamine / CH₂Cl₂ / 3 h / -78 - 20 °C

7.1: 46 percent / H₂ / Pd/C / tetrahydrofuran

8.1: Jones reagent / acetone / 2 h / cooling

8.2: HOBt; EDCl / CH₂Cl₂ / 20 °C

8.3: tin(II) chloride; acetyl chloride / dimethylformamide / 1 h / 20 °C

9.1: iodomethylsilane; 2,6-ditert-butyl-4-methylpyridine / acetonitrile / 5 h / cooling

With 2,6-di-tert-butyl-4-methylpyridine; jones reagent; (iodomethyl)silane; potassium trimethylsilonate; hydrogen; acetic acid; triethylamine; N-Trimethylsilylacetamide; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetone; acetonitrile; butanone;

DOI:10.1021/ja038445l

upstream raw materials:

3-{3-(4-acetylamino-4-tert-butoxycarbonyl-butyrylamino)-3-[1-(1-tert-butoxycarbonyl-ethylcarbamoyl)-ethylcarbamoyl]-propyl}-7-tert-butoxycarbonylamino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

4-methoxybenzyl-7-amino-3-chloromethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride

3-chloromethyl-7β-tert-butylcarbonylamino-3-cephem-4-carboxylic acid p-methoxybenzyl ester

4-methoxybenzyl 7β-t-butoxycarbonylamino-3-iodomethyl-3-cephemcarboxylate

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