3-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-5,6-dihydro-2(1H)-pyridinone

Base Information

• Chemical Name: 3-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-5,6-dihydro-2(1H)-pyridinone
• CAS No.: 130291-51-9
• Molecular Formula: C₂₂H₃₀N₂O₇S
• Molecular Weight: 466.555

Synonyms:3-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-5,6-dihydro-2(1H)-pyridinone

Chemical Property of 3-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-5,6-dihydro-2(1H)-pyridinone

Chemical Property:

Purity/Quality:

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Technology Process of 3-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-5,6-dihydro-2(1H)-pyridinone

There total 6 articles about 3-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-5,6-dihydro-2(1H)-pyridinone 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: 80.0%

2-(tert-Butoxycarbonyl-methyl-amino)-3-[2-oxo-3-phenylsulfanyl-1-(toluene-4-sulfonyl)-piperidin-3-yl]-propionic acid methyl ester (130291-49-5) → 3-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-5,6-dihydro-2(1H)-pyridinone (130291-51-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/S0040-4039(00)94730-0

Reference yield:

N-Boc-N-methyl-dehydroalanine methyl ester (56776-34-2) → 3-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-5,6-dihydro-2(1H)-pyridinone (130291-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) 18-crown-6, KN(TMS)2 / 1) THF, toluene, -25 deg C, 5 min, 2) -25 deg C, 1 h

2: 80 percent / m-CPBA, aq.NaHCO₃ / CH₂Cl₂ / 0 °C

With 18-crown-6 ether; potassium hexamethylsilazane; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jo00047a031

Reference yield:

N-(p-Toluenesulfonyl)-3-(phenylthio)-2-piperidone (143076-20-4) → 3-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-5,6-dihydro-2(1H)-pyridinone (130291-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) 18-crown-6, KN(TMS)2 / 1) THF, toluene, -25 deg C, 5 min, 2) -25 deg C, 1 h

2: 80 percent / m-CPBA, aq.NaHCO₃ / CH₂Cl₂ / 0 °C

With 18-crown-6 ether; potassium hexamethylsilazane; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jo00047a031

upstream raw materials:

2-(tert-Butoxycarbonyl-methyl-amino)-3-[2-oxo-3-phenylsulfanyl-1-(toluene-4-sulfonyl)-piperidin-3-yl]-propionic acid methyl ester

N-tert-butoxycarbonylserine methyl ester

methyl 2-[(tert-butoxycarbonyl)amino]acrylate

N-Boc-N-methyl-dehydroalanine methyl ester

Downstream raw materials:

rac-Methyl (2S^*,3aS^*,6aS^*,10aS^*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate

rac-Methyl (2R^*,3aS^*,6aS^*,10aS^*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate

rac-Methyl (2R^*,3aS^*,6aS^*,10aS^*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate 5-ethylene ketal

2-(tert-Butoxycarbonyl-methyl-amino)-3-[(4aR,8aR)-1,6-dioxo-2-(toluene-4-sulfonyl)-2,3,4,4a,5,6-hexahydro-1H-isoquinolin-8a-yl]-propionic acid methyl ester

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