methyl (1aR,7bS)-5-{2-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]-4-fluorobenzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate

Base Information

• Chemical Name: methyl (1aR,7bS)-5-{2-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]-4-fluorobenzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate
• CAS No.: 1609201-04-8
• Molecular Formula: C₂₅H₂₈FNO₇S
• Molecular Weight: 505.564
• Mol file: 1609201-04-8.mol

Synonyms:methyl (1aR,7bS)-5-{2-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]-4-fluorobenzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate

Chemical Property of methyl (1aR,7bS)-5-{2-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]-4-fluorobenzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1aR,7bS)-5-{2-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]-4-fluorobenzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate

There total 11 articles about methyl (1aR,7bS)-5-{2-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]-4-fluorobenzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-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:

methyl (1aR,7bS)-5-amino-1,1 a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (1412976-22-7) + 2-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]-4-fluorobenzenesulfonyl chloride (1609201-05-9) → methyl (1aR,7bS)-5-{2-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]-4-fluorobenzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (1609201-04-8)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 17h;

Reference yield:

2-bromo-5-fluorobenzyl bromide (112399-50-5) → methyl (1aR,7bS)-5-{2-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]-4-fluorobenzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (1609201-04-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydroxide / toluene / 20 h / 60 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / toluene / 3 h / Dean-Stark; Reflux

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 - 20 °C

3.3: 0.5 h / 20 °C

4.1: pyridine / dichloromethane / 17 h / 20 °C

With pyridine; n-butyllithium; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; sodium hydroxide; In tetrahydrofuran; hexane; dichloromethane; toluene;

Reference yield:

methyl 5-(2,2-dimethylpropionylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (1412976-20-5) → methyl (1aR,7bS)-5-{2-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]-4-fluorobenzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (1609201-04-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / methanol / 60 h / Inert atmosphere; Reflux

2: Lux C-3 column / methanol; diethylamine; carbon dioxide / Supercritical conditions; liquid CO₂

3: pyridine / dichloromethane / 17 h / 20 °C

With pyridine; sulfuric acid; In methanol; dichloromethane; carbon dioxide; diethylamine;

upstream raw materials:

2-bromo-5-fluorobenzyl bromide

methyl (1aR,7bS)-5-amino-1,1 a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

2-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]-4-fluorobenzenesulfonyl chloride

methyl 5-(2,2-dimethylpropionylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

Downstream raw materials:

methyl (1aR,7bS)-5-[2-(3-diethylamino-2,2-dimethylpropyl)-4-fluorobenzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

(1aR,7bS)-5-[2-(3-diethylamino-2,2-dimethylpropyl)-4-fluorobenzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid