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

Base Information

• Chemical Name: 2-(tert-Butoxycarbonyl-methyl-amino)-3-[2-oxo-3-phenylsulfanyl-1-(toluene-4-sulfonyl)-piperidin-3-yl]-propionic acid methyl ester
• CAS No.: 130291-49-5
• Molecular Formula: C₂₈H₃₆N₂O₇S₂
• Molecular Weight: 576.735
• Mol file: 130291-49-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 2-(tert-Butoxycarbonyl-methyl-amino)-3-[2-oxo-3-phenylsulfanyl-1-(toluene-4-sulfonyl)-piperidin-3-yl]-propionic acid methyl 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: 60.0%

N-Boc-N-methyl-dehydroalanine methyl ester (56776-34-2) + N-(p-Toluenesulfonyl)-3-(phenylthio)-2-piperidone (143076-20-4) → 2-(tert-Butoxycarbonyl-methyl-amino)-3-[2-oxo-3-phenylsulfanyl-1-(toluene-4-sulfonyl)-piperidin-3-yl]-propionic acid methyl ester (130291-49-5)

Guidance literature:

With potassium hexamethylsilazane;

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

Reference yield:

N-tert-butoxycarbonylserine methyl ester (69942-12-7) → 2-(tert-Butoxycarbonyl-methyl-amino)-3-[2-oxo-3-phenylsulfanyl-1-(toluene-4-sulfonyl)-piperidin-3-yl]-propionic acid methyl ester (130291-49-5)

Guidance literature:

Multi-step reaction with 3 steps

1: via elimination of its mesylate

2: 81.5 percent / Ag₂O / dimethylformamide / Ambient temperature

3: 1) 18-crown-6, KN(TMS)2 / 1) THF, toluene, -25 deg C, 5 min, 2) -25 deg C, 1 h

With 18-crown-6 ether; potassium hexamethylsilazane; silver(l) oxide; In N,N-dimethyl-formamide;

DOI:10.1021/jo00047a031

Reference yield:

methyl 2-[(tert-butoxycarbonyl)amino]acrylate (55477-80-0) → 2-(tert-Butoxycarbonyl-methyl-amino)-3-[2-oxo-3-phenylsulfanyl-1-(toluene-4-sulfonyl)-piperidin-3-yl]-propionic acid methyl ester (130291-49-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 81.5 percent / Ag₂O / dimethylformamide / Ambient temperature

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

With 18-crown-6 ether; potassium hexamethylsilazane; silver(l) oxide; In N,N-dimethyl-formamide;

DOI:10.1021/jo00047a031

upstream raw materials:

N-Boc-N-methyl-dehydroalanine methyl ester

N-(p-Toluenesulfonyl)-3-(phenylthio)-2-piperidone

N-tert-butoxycarbonylserine methyl ester

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

Downstream raw materials:

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

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

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 (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