Lapaquistat

Base Information

• Chemical Name: Lapaquistat
• CAS No.: 189059-71-0
• Molecular Formula: C31H39ClN2O8
• Molecular Weight: 603.112
• UNII: PEZ79BV72X
• Wikipedia: Lapaquistat
• Wikidata: Q6488102
• NCI Thesaurus Code: C96287
• Pharos Ligand ID: DVWGK5J4KFAA
• ChEMBL ID: CHEMBL341976
• Mol file: 189059-71-0.mol

Synonyms:(1-(2-(1-(2-carboxyoxy-1,1-dimethylethyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydrobenzo(e)(1,4)oxazepin-3-yl)acetyl)piperidin-4-yl)acetic acid;1-((1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl)acetyl)piperidine-4-acetic acid;lapaquistat;TAK 475;TAK-475;TAK475

Chemical Property of Lapaquistat

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 824.024°C at 760 mmHg
• Flash Point: 452.154°C
• PSA: 125.84000
• Density: 1.261g/cm³
• LogP: 4.30320
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 602.2394939
• Heavy Atom Count: 42
• Complexity: 942

Purity/Quality:

99% ^*data from raw suppliers

Lapaquistat 99.79% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(CN1C2=C(C=C(C=C2)Cl)C(OC(C1=O)CC(=O)N3CCC(CC3)CC(=O)O)C4=C(C(=CC=C4)OC)OC)CO
• Isomeric SMILES: CC(C)(CN1C2=C(C=C(C=C2)Cl)[C@H](O[C@@H](C1=O)CC(=O)N3CCC(CC3)CC(=O)O)C4=C(C(=CC=C4)OC)OC)CO
• Recent EU Clinical Trials: A Double-Blind, Randomized Study to Evaluate the Efficacy and Safety of Lapaquistat Acetate 50 mg versus Placebo in Subjects with Hypercholesterolemia, With an Optional Open-Label Extension

Technology Process of Lapaquistat

There total 8 articles about Lapaquistat 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: 70.0%

ethyl 1-[[(3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidine-4-acetate (189059-65-2) → N-[[(3R,5S)-1-(3-hydroxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidine-4-acetic acid (189059-71-0)

Guidance literature:

With sodium hydroxide; In ethanol; at 60 ℃; for 0.5h;

DOI:10.1021/jm020234o

Reference yield:

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) → N-[[(3R,5S)-1-(3-hydroxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidine-4-acetic acid (189059-71-0)

Guidance literature:

Multi-step reaction with 7 steps

1: AcOH / methanol / 1 h / 60 °C

2: NaBH₃CN / methanol / 2 h / 60 °C

3: 100 percent / NaHCO₃ / ethyl acetate / 0.5 h / 20 °C

4: 79 percent / K₂CO₃ / ethanol / 20 °C

5: 94 percent / aq. NaOH / ethanol / 2 h / 60 °C

6: 57 percent / diethylphosphoryl cyanide; Et₃N / dimethylformamide / 0.5 h / 20 °C

7: 70 percent / 1N aq. NaOH / ethanol / 0.5 h / 60 °C

With sodium hydroxide; diethylphosphoryl cyanide; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; In methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm020234o

Reference yield:

(-)-2-amino-5-chloro-α-(2,3-dimethoxyphenyl)benzyl alcohol (189059-58-3) → N-[[(3R,5S)-1-(3-hydroxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidine-4-acetic acid (189059-71-0)

Guidance literature:

Multi-step reaction with 7 steps

1: AcOH / methanol / 1 h / 60 °C

2: NaBH₃CN / methanol / 2 h / 60 °C

3: 100 percent / NaHCO₃ / ethyl acetate / 0.5 h / 20 °C

4: 79 percent / K₂CO₃ / ethanol / 20 °C

5: 94 percent / aq. NaOH / ethanol / 2 h / 60 °C

6: 57 percent / diethylphosphoryl cyanide; Et₃N / dimethylformamide / 0.5 h / 20 °C

7: 70 percent / 1N aq. NaOH / ethanol / 0.5 h / 60 °C

With sodium hydroxide; diethylphosphoryl cyanide; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; In methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm020234o

upstream raw materials:

ethyl 1-[[(3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidine-4-acetate

2,2-dimethyl-3-hydroxypropionaldehyde

(-)-2-amino-5-chloro-α-(2,3-dimethoxyphenyl)benzyl alcohol

(S)-5-chloro-α-(2,3-dimethoxyphenyl)-2-(3-hydroxy-2,2-dimethylpropyl)aminobenzyl alcohol

Downstream raw materials:

benzyl 1-[[(3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-[2,2-dimethyl-3-(pivaloyloxymethyloxy)propyl]-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidine-4-acetate

benzyl 1-[[(3R,5S)-1-[3-(butyryloxy)-2,2-dimethylpropyl]-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidine-4-acetate

benzyl 1-[[(3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-[2,2-dimethyl-3-(propionyloxy)propyl]-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidine-4-acetate

benzyl 1-[[(3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-[2,2-dimethyl-3-(isobutyryloxy)propyl]-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidine-4-acetate