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

Base Information

• Chemical Name: 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
• CAS No.: 130291-54-2
• Molecular Formula: C₂₆H₃₄N₂O₈S
• Molecular Weight: 534.631
• Mol file: 130291-54-2.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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:

N-Boc-N-methyl-dehydroalanine methyl ester (56776-34-2) → 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 (130291-54-2,143076-17-9,143076-25-9)

Guidance literature:

Multi-step reaction with 3 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

3: 2) camphorsulfonic acid / 1) toluene, 11 kbar, r.t., 90 h, 2) THF, r.t., 1 h

With 18-crown-6 ether; camphor-10-sulfonic acid; 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) → 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 (130291-54-2,143076-17-9,143076-25-9)

Guidance literature:

Multi-step reaction with 3 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

3: 2) camphorsulfonic acid / 1) toluene, 11 kbar, r.t., 90 h, 2) THF, r.t., 1 h

With 18-crown-6 ether; camphor-10-sulfonic acid; potassium hexamethylsilazane; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jo00047a031

Reference yield:

2-(tert-Butoxycarbonyl-methyl-amino)-3-[2-oxo-3-phenylsulfanyl-1-(toluene-4-sulfonyl)-piperidin-3-yl]-propionic acid methyl ester (130291-49-5) → 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 (130291-54-2,143076-17-9,143076-25-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / m-CPBA, aq.NaHCO₃ / CH₂Cl₂ / 0 °C

2: 2) camphorsulfonic acid / 1) toluene, 11 kbar, r.t., 90 h, 2) THF, r.t., 1 h

With camphor-10-sulfonic acid; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jo00047a031

upstream raw materials:

danishefsky's diene

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

N-tert-butoxycarbonylserine methyl ester

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

Downstream raw materials:

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 (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