Tert-butyl (E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-YL]-5-hydroxy-3-oxo-6-heptenoate

Base Information

• Chemical Name: Tert-butyl (E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-YL]-5-hydroxy-3-oxo-6-heptenoate
• CAS No.: 375846-25-6
• Molecular Formula: C28H32FNO4
• Molecular Weight: 465.565
• European Community (EC) Number: 609-442-4
• DSSTox Substance ID: DTXSID101110267
• Mol file: 375846-25-6.mol

Synonyms:375846-25-6;194934-95-7;TERT-BUTYL (E)-7-[3-(4-FLUOROPHENYL)-1-(1-METHYLETHYL)-1H-INDOL-2-YL]-5-HYDROXY-3-OXO-6-HEPTENOATE;(E)-tert-Butyl 7-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-5-hydroxy-3-oxohept-6-enoate;tert-butyl (E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-5-hydroxy-3-oxohept-6-enoate;fhh: fluvastatin intermediate;SCHEMBL4906083;SCHEMBL6773187;O-tert-Butyl-3-keto Fluvastatin;DTXSID101110267;2-Methyl-2-propanyl (6E)-7-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoate;BCP28674;tert-butyl (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-5-hydroxy-3-oxohept-6-enoate;AKOS015897014;AC-26813;A823770;(6E)-7-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoic Acid 1,1-Dimethylethyl Ester;(E)-tert-Butyl7-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-5-hydroxy-3-oxohept-6-enoate;1,1-Dimethylethyl (6E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoate;7-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoic acid 1,1-dimethylethyl ester;tert-Butyl(E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoate

Chemical Property of Tert-butyl (E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-YL]-5-hydroxy-3-oxo-6-heptenoate

Chemical Property:

• Boiling Point: 647.7 °C at 760 mmHg
• PKA: 10.35±0.46(Predicted)
• Flash Point: 345.5 °C
• PSA: 68.53000
• Density: 1.13 g/cm³
• LogP: 6.09340
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 465.23153666
• Heavy Atom Count: 34
• Complexity: 722

Purity/Quality:

99% ^*data from raw suppliers

(6E)-7-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoicAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N1C2=CC=CC=C2C(=C1C=CC(CC(=O)CC(=O)OC(C)(C)C)O)C3=CC=C(C=C3)F
• Isomeric SMILES: CC(C)N1C2=CC=CC=C2C(=C1/C=C/C(CC(=O)CC(=O)OC(C)(C)C)O)C3=CC=C(C=C3)F
• Uses: (6E)-7-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoic Acid 1,1-Dimethylethyl Ester is an intermediate in the synthesis of metabolite of Fluvastatin (F601250), a synthetic HMG-CoA reductase inhibitor used as an antilipemic agent.

Technology Process of Tert-butyl (E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-YL]-5-hydroxy-3-oxo-6-heptenoate

There total 4 articles about Tert-butyl (E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-YL]-5-hydroxy-3-oxo-6-heptenoate 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: 98.8%

tert-butyl acetoacetate (1694-31-1) + 3-<3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl>-2(E)-propenal (93957-50-7) → 7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoic acid-1,1-dimethylethyl ester (375846-25-6)

Guidance literature:

tert-butyl acetoacetate; With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; paraffin oil; at 0 - 25 ℃; Inert atmosphere;

3-<3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl>-2(E)-propenal; In tetrahydrofuran; hexane; paraffin oil; at 0 ℃; Inert atmosphere;

DOI:10.1021/op060191b

Reference yield: 91.1%

n-butyllithium (109-72-8,29786-93-4) + tert-butyl acetoacetate (1694-31-1) + 3-<3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl>-2(E)-propenal (93957-50-7) → 7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoic acid-1,1-dimethylethyl ester (375846-25-6)

Guidance literature:

tert-butyl acetoacetate; With sodium hydride; In hexane; at 0 ℃; for 0.5h; Inert atmosphere; Large scale;

n-butyllithium; In hexane; for 1h; Large scale;

3-<3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl>-2(E)-propenal; In hexane; at -10 ℃; for 2h; Solvent; Temperature; Large scale;

Reference yield: 85.0%

tert-butyl acetoacetate (1694-31-1) + 3-<3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl>-2(E)-propenal (93957-50-7) → 7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoic acid-1,1-dimethylethyl ester (375846-25-6) + (4E,6E)-7-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-oxo-hepta-4,6-dienoic acid tert-butyl ester + (E)-6-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-4-hydroxy-hex-5-en-2-one + 6-{(E)-2-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-vinyl}-4-hydroxy-5,6-dihydro-pyran-2-one

Guidance literature:

tert-butyl acetoacetate; With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; paraffin oil; at 0 - 25 ℃; Inert atmosphere;

3-<3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl>-2(E)-propenal; In tetrahydrofuran; hexane; paraffin oil; at 0 ℃; Inert atmosphere;

With water; at 0 ℃; Temperature;

DOI:10.1021/op060191b

upstream raw materials:

(E)-5-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-hydroxypent-4-enoic acid methyl ester

acetic acid tert-butyl ester

tert-butyl acetoacetate

3-<3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl>-2(E)-propenal

Downstream raw materials:

R*,S*-(E)-(+/-)-3,5-dihydroxy-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-6-heptenoic acid tert-butyl ester

Refernces

• 1、 Fuenfschilling, Peter C.,Hoehn, Pascale,Mutz, Jean-Paul. "An Improved Manufacturing Process for Fluvastatin". . p. 13 - 18. Retrieved 2012/12/26.