Ethyl 5-((S)-2-(benzyloxycarbonylamino)-3-methoxy-3-oxopropyl)-2-(methoxy(methyl)-carbamoyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

Base Information

• Chemical Name: Ethyl 5-((S)-2-(benzyloxycarbonylamino)-3-methoxy-3-oxopropyl)-2-(methoxy(methyl)-carbamoyl)-3,4-dihydro-2H-pyrrole-2-carboxylate
• CAS No.: 1428260-99-4
• Molecular Formula: C₂₂H₂₉N₃O₈
• Molecular Weight: 463.488

Synonyms:Ethyl 5-((S)-2-(benzyloxycarbonylamino)-3-methoxy-3-oxopropyl)-2-(methoxy(methyl)-carbamoyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

Chemical Property of Ethyl 5-((S)-2-(benzyloxycarbonylamino)-3-methoxy-3-oxopropyl)-2-(methoxy(methyl)-carbamoyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ethyl 5-((S)-2-(benzyloxycarbonylamino)-3-methoxy-3-oxopropyl)-2-(methoxy(methyl)-carbamoyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

There total 9 articles about Ethyl 5-((S)-2-(benzyloxycarbonylamino)-3-methoxy-3-oxopropyl)-2-(methoxy(methyl)-carbamoyl)-3,4-dihydro-2H-pyrrole-2-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: 49.0%

(2S)-8-ethyl N-(benzyloxycarbonyl) 1-methyl-2-(tosyloxyimino)-7-(2-methoxypropanoyl)-4-oxooctanedioate (1428261-09-9) → Ethyl 5-((S)-2-(benzyloxycarbonylamino)-3-methoxy-3-oxopropyl)-2-(methoxy(methyl)-carbamoyl)-3,4-dihydro-2H-pyrrole-2-carboxylate (1428260-99-4) + Methyl N-carbobenzyloxy-3-(4-ethoxy-3-(methoxy(methyl)carbamoyl)-4-oxobutyl)-4,5-dihydro-1H-pyrazole-5-carboxylate (1428261-00-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 0.5h; Reflux;

DOI:10.1016/j.tetlet.2013.01.130

Reference yield:

N-Cbz-L-Asp (1152-61-0) → Ethyl 5-((S)-2-(benzyloxycarbonylamino)-3-methoxy-3-oxopropyl)-2-(methoxy(methyl)-carbamoyl)-3,4-dihydro-2H-pyrrole-2-carboxylate (1428260-99-4) + Methyl N-carbobenzyloxy-3-(4-ethoxy-3-(methoxy(methyl)carbamoyl)-4-oxobutyl)-4,5-dihydro-1H-pyrazole-5-carboxylate (1428261-00-0)

Guidance literature:

Multi-step reaction with 9 steps

1: toluene-4-sulfonic acid / toluene / 2 h / Reflux

2: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 2 h / 20 °C

3: trans benzyl(chloro)bis(triphenylphosphine)palladium(II) / toluene / 3 h / Reflux

4: caesium carbonate / dichloromethane / 1 h / Reflux

5: sodium hydrogencarbonate / methanol / 0.17 h / Reflux

6: thionyl chloride / 20 °C

7: hydroxylamine hydrochloride; triethylamine / ethanol / 1 h / Reflux

8: triethylamine / dichloromethane / 3 h / 20 °C

9: sodium hydride / tetrahydrofuran / 0.5 h / Reflux

With thionyl chloride; oxalyl dichloride; trans benzyl(chloro)bis(triphenylphosphine)palladium(II); hydroxylamine hydrochloride; sodium hydride; sodium hydrogencarbonate; caesium carbonate; toluene-4-sulfonic acid; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene;

DOI:10.1016/j.tetlet.2013.01.130

Reference yield:

(4S)-3-benzyloxycarbonyl-4-carboxymethyl-1,3-oxazolidin-5-one (23632-66-8) → Ethyl 5-((S)-2-(benzyloxycarbonylamino)-3-methoxy-3-oxopropyl)-2-(methoxy(methyl)-carbamoyl)-3,4-dihydro-2H-pyrrole-2-carboxylate (1428260-99-4) + Methyl N-carbobenzyloxy-3-(4-ethoxy-3-(methoxy(methyl)carbamoyl)-4-oxobutyl)-4,5-dihydro-1H-pyrazole-5-carboxylate (1428261-00-0)

Guidance literature:

Multi-step reaction with 8 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 2 h / 20 °C

2: trans benzyl(chloro)bis(triphenylphosphine)palladium(II) / toluene / 3 h / Reflux

3: caesium carbonate / dichloromethane / 1 h / Reflux

4: sodium hydrogencarbonate / methanol / 0.17 h / Reflux

5: thionyl chloride / 20 °C

6: hydroxylamine hydrochloride; triethylamine / ethanol / 1 h / Reflux

7: triethylamine / dichloromethane / 3 h / 20 °C

8: sodium hydride / tetrahydrofuran / 0.5 h / Reflux

With thionyl chloride; oxalyl dichloride; trans benzyl(chloro)bis(triphenylphosphine)palladium(II); hydroxylamine hydrochloride; sodium hydride; sodium hydrogencarbonate; caesium carbonate; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene;

DOI:10.1016/j.tetlet.2013.01.130

upstream raw materials:

Ethyl N-(benzyloxycarbonyl)2-(methoxy(methyl)carbamoyl)-5-oxo-6-((S)-5-oxooxazolidin-4-yl)hexanoate

(2S)-8-ethyl N-(benzyloxycarbonyl) 1-methyl-2-amino-7-(2-methoxypropanoyl)-4-oxooctanedioate

(2S)-8-ethyl N-(benzyloxycarbonyl)-1-methyl-2-(hydroxyimino)-7-(2-ethoxypropanoyl)-4-oxooctanedioate

N-Cbz-L-Asp

Downstream raw materials:

Ethyl 5-((S)-2-(benzyloxycarbonylamino)-3-methoxy-3-oxopropyl)-2-(methoxy(methyl)-carbamoyl)pyrrolidine-2-carboxylate

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