Cyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxylic acid, 2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydro-2-[[7-Methoxy-8-Methyl-2-[4-(1-Methylethyl)-2-thiazolyl]-4-quinolinyl]oxy]-5-Methyl-4,14-dioxo-, (2R,3aR,10Z,11aS,12aR,14aR)-

Base Information

• Chemical Name: Cyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxylic acid, 2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydro-2-[[7-Methoxy-8-Methyl-2-[4-(1-Methylethyl)-2-thiazolyl]-4-quinolinyl]oxy]-5-Methyl-4,14-dioxo-, (2R,3aR,10Z,11aS,12aR,14aR)-
• CAS No.: 923604-58-4
• Molecular Formula: C₃₅H₄₂N₄O₆S
• Molecular Weight: 646.808
• Mol file: 923604-58-4.mol

Synonyms:Cyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxylic acid, 2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydro-2-[[7-Methoxy-8-Methyl-2-[4-(1-Methylethyl)-2-thiazolyl]-4-quinolinyl]oxy]-5-Methyl-4,14-dioxo-, (2R,3aR,10Z,11aS,12aR,14aR)-;(2R,3aR,10Z,11aS,12aR,14aR)-2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-Tetradecahydro-2-[[7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]-4-quinolinyl]oxy]-5-methyl-4,14-dioxocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxylic acid;(2R,3aR,10Z,11aS,12aR,14aR)-

Chemical Property of Cyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxylic acid, 2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydro-2-[[7-Methoxy-8-Methyl-2-[4-(1-Methylethyl)-2-thiazolyl]-4-quinolinyl]oxy]-5-Methyl-4,14-dioxo-, (2R,3aR,10Z,11aS,12aR,14aR)-

Chemical Property:

• Vapor Pressure: 0-0Pa at 20-25℃
• PKA: 3.48±0.40(Predicted)
• PSA: 159.19000
• Density: 1.251±0.06 g/cm3(Predicted)
• LogP: 5.99700

Purity/Quality:

99.9% ^*data from raw suppliers

Cyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxylicacid,2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydro-2-[[7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]-4-quinolinyl]oxy]-5-methyl-4,14-dioxo-,(2R,3aR,10Z,11aS,12aR,14aR)- ≥97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxylic acid, 2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydro-2-[[7-Methoxy-8-Methyl-2-[4-(1-Methylethyl)-2-thiazolyl]-4-quinolinyl]oxy]-5-Methyl-4,14-dioxo-, (2R,3aR,10Z,11aS,12aR,14aR)-

There total 12 articles about Cyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxylic acid, 2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydro-2-[[7-Methoxy-8-Methyl-2-[4-(1-Methylethyl)-2-thiazolyl]-4-quinolinyl]oxy]-5-Methyl-4,14-dioxo-, (2R,3aR,10Z,11aS,12aR,14aR)- 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:

(1R,4R,5R)-N-(hex-5-en-1-yl)-N-methyl-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamide (862174-98-9) → (2R,3aR,10Z,11aS,12aR,14aR)-2-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)-5-methyl-4,14-dioxo-2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxylic acid (923604-58-4)

Guidance literature:

Multi-step reaction with 6 steps

1: methanesulfonic acid / 20 h / 60 °C / pH 2 / Reflux

2: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 2 h / -2 - 0 °C / Large scale

3: lithium hydroxide monohydrate / water; tetrahydrofuran / 24 h / 20 °C

4: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / water; tetrahydrofuran / 24 h / 20 °C

5: methanesulfonic acid; Hoveyda-Grubbs catalyst first generation / 1,2-dichloro-ethane / 6 h / Inert atmosphere; Reflux; Large scale

6: sodium hydroxide / water; ethanol / 10 h / Reflux

With Hoveyda-Grubbs catalyst first generation; methanesulfonic acid; lithium hydroxide monohydrate; di-isopropyl azodicarboxylate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; ethanol; water; 1,2-dichloro-ethane; toluene;

DOI:10.1021/acs.joc.8b03124

Reference yield:

methyl (1R,2R,4R)-2-[5-hexen-1-yl-(methyl)carbamoyl]-4-hydroxycyclopentanecarboxylate (1042695-84-0) → (2R,3aR,10Z,11aS,12aR,14aR)-2-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)-5-methyl-4,14-dioxo-2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxylic acid (923604-58-4)

Guidance literature:

Multi-step reaction with 5 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 2 h / -2 - 0 °C / Large scale

2: lithium hydroxide monohydrate / water; tetrahydrofuran / 24 h / 20 °C

3: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / water; tetrahydrofuran / 24 h / 20 °C

4: methanesulfonic acid; Hoveyda-Grubbs catalyst first generation / 1,2-dichloro-ethane / 6 h / Inert atmosphere; Reflux; Large scale

5: sodium hydroxide / water; ethanol / 10 h / Reflux

With Hoveyda-Grubbs catalyst first generation; methanesulfonic acid; lithium hydroxide monohydrate; di-isopropyl azodicarboxylate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; ethanol; water; 1,2-dichloro-ethane; toluene;

DOI:10.1021/acs.joc.8b03124

Reference yield:

methyl (1R,2R,4S)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentane-1-carboxylate → (2R,3aR,10Z,11aS,12aR,14aR)-2-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)-5-methyl-4,14-dioxo-2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxylic acid (923604-58-4)

Guidance literature:

Multi-step reaction with 4 steps

1: lithium hydroxide monohydrate / water; tetrahydrofuran / 24 h / 20 °C

2: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / water; tetrahydrofuran / 24 h / 20 °C

3: methanesulfonic acid; Hoveyda-Grubbs catalyst first generation / 1,2-dichloro-ethane / 6 h / Inert atmosphere; Reflux; Large scale

4: sodium hydroxide / water; ethanol / 10 h / Reflux

With Hoveyda-Grubbs catalyst first generation; methanesulfonic acid; lithium hydroxide monohydrate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; sodium hydroxide; In tetrahydrofuran; ethanol; water; 1,2-dichloro-ethane;

DOI:10.1021/acs.joc.8b03124

upstream raw materials:

(1R,4R,5R)-N-(hex-5-en-1-yl)-N-methyl-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamide

methyl (1R,2R,4R)-2-[5-hexen-1-yl-(methyl)carbamoyl]-4-hydroxycyclopentanecarboxylate

ethyl (1R,2S)-2-ethenyl-1-({[(1R,2R,4R)-2-[hex-5-en-1-yl-(methyl)carbamoyl]-4-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)cyclopentyl]carbonyl}-amino)cyclopropanecarboxylate

rac-4-oxocyclopentane-1,2-dicarboxylic acid

Downstream raw materials:

simeprevir

Refernces