ledipasvir interMediate

Base Information

• Chemical Name: ledipasvir interMediate
• CAS No.: 1441670-89-8
• Molecular Formula: C27H26BrF2N3O2
• Molecular Weight: 542.4150464
• Mol file: 1441670-89-8.mol

Synonyms:(S)-tert-butyl 6-(5-(7-broMo-9,9-difluoro-9H-fluoren-2-yl)-1H-iMidazol-2-yl)-5-azaspiro[2.4]heptane-5-carboxylate;5-Azaspiro[2.4]heptane-5-carboxylic acid, 6-[5-(7-broMo-9,9-difluoro-9H-fluoren-2-yl)-1H-iMidazol-2-yl]-, 1,1-diMethylethyl ester, (6S)-;(6S)-6-[5-(7-Bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptane-5-carboxylic acid 1,1-dimethylethyl ester;(6S)-tert-butyl-6-(5-(7-broMo-9,9-difluoro-9H-fluoren-2-yl)-1H-iMidazol-2-yl)-5-azaspiro[2.4]heptane-5-carboxylate;InterMediate of Ledipasvir;(6S)-6-[5-(7-Bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptane-5-carboxylic acid 1,1-dimethylester;Ledipasvir INT 3;ledipasvir interMediate ,(6S)-6-[5-(7-BroMo-9,9-difluoro-9H-fluoren-2-yl)-1H-iMidazol-2-yl]-5-azaspiro[2.4]heptane-5-carboxylic acid 1,1-diMethylethyl ester

Chemical Property of ledipasvir interMediate

Chemical Property:

• Boiling Point: 681.1±55.0 °C(Predicted)
• PKA: 11.13±0.10(Predicted)
• PSA: 58.22000
• Density: 1.53±0.1 g/cm3(Predicted)
• LogP: 7.35970
• Storage Temp.: 2-8°C

Purity/Quality:

98%min. ^*data from raw suppliers

(6S)-tert-butyl-6-(5-(7-broMo-9,9-difluoro-9H-fluoren-2-yl)-1H-iMidazol-2-yl)-5-azaspiro[2.4]heptane-5-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ledipasvir interMediate

There total 14 articles about ledipasvir interMediate 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: 87.0%

(S)-6-(2-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-2-oxoethyl) 5-tert-butyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate (1499193-61-1) → (6S)-6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptane-5-carboxylic acid 1,1-dimethylethyl ester (1441670-89-8)

Guidance literature:

With ammonium acetate; In ethanol; 2-methoxy-ethanol; toluene; at 90 ℃; for 18h;

Reference yield: 77.0%

(S)-6-(2-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-2-oxoethyl) 5-tert-butyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate (1499193-61-1) + ammonium acetate (631-61-8,92206-38-7) → (6S)-6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptane-5-carboxylic acid 1,1-dimethylethyl ester (1441670-89-8)

Guidance literature:

In 2-methoxy-ethanol; toluene; at 90 ℃;

Reference yield:

(6S)-5-[(tert-butoxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acid (1129634-44-1,1454843-77-6,1454843-78-7) → (6S)-6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptane-5-carboxylic acid 1,1-dimethylethyl ester (1441670-89-8)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium tert-butylate / 2-methyltetrahydrofuran; tetrahydrofuran / 3 h / 20 - 40 °C

2: acetone / 55 °C

3: ammonium acetate / toluene; 2-methoxy-ethanol / 90 °C

With potassium tert-butylate; ammonium acetate; In tetrahydrofuran; 2-methyltetrahydrofuran; 2-methoxy-ethanol; acetone; toluene;

upstream raw materials:

(6S)-5-[(tert-butoxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acid

[1-(hydroxymethyl)cyclopropyl]methanol

1,1-bis(iodomethyl)cyclopropane

cyclopropane-1,1-diylbis(methylene) dimethanesulfonate

Downstream raw materials:

methyl [(2S)-1-{(6S)-6-[5-(9,9-difluoro-7-{2-[(1R,3S,4S)-2-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-azabicyclo[2.2.1]-hept-3-yl]-1H-benzimidazol-6-yl}-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]hept-5-yl}-3-methyl-1-oxobutan-2-yl]carbamate

(1-{3-[6-(9,9-difluoro-7-{2-[5-(2-methoxycarbonylamino-3-methyl-butyryl)-5-aza-spiro[2.4]hept-6-yl]-3H-imidazol-4-yl}-9H-fluoren-2-yl)-1H-benzoimidazol-2-yl]2-aza-bicyclo[2.2.1]heptane-2-carbonyl}-2-methyl-propyl)carbamicacid methyl ester D-tartrate salt

(1-{6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-aza-spiro[2.4]heptane-5-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester