Tert-buthyl Pitavastatin Chemical Properties

Boiling point:

674.5±55.0 °C(Predicted)

Density 

1.235±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform (Sligthly), Methanol (Slightly)

form 

Solid

pka

13.52±0.20(Predicted)

color 

White to Off-White

InChIKey

RCARMBIYAHBUHR-UQECUQMJSA-N

SMILES

C(OC(C)(C)C)(=O)C[C@H](O)C[C@H](O)/C=C/C1=C(C2=CC=C(F)C=C2)C2C(N=C1C1CC1)=CC=CC=2

Tert-buthyl Pitavastatin Usage And Synthesis

Uses

tert-Butyl Pitavastatin is used to prepare hemicalcium salt.

Synthesis

Tert-butyl (4R,6S)-6-[[(1E)-2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]vinyl]-2,2-dimethyl-1,3-dioxane-4-acetate (1.5 kg) was used as raw material and dissolved in acetonitrile (16 L). A mixture of 35% HCl solution (0.91 kg) and purified water (9.5 kg) was slowly added under stirring conditions over a period of 2 hours. Stirring of the reaction mixture was continued for 1 hour. The progress of the reaction was monitored by HPLC and the reaction was terminated after confirming complete consumption of the raw material. The reaction mixture was neutralized with sodium bicarbonate and subsequently extracted with ethyl acetate. The organic layer was separated, washed with sodium chloride solution (1.5 kg) and concentrated under reduced pressure. The concentrated residue was dissolved in ethyl acetate (1.5 L) and hexane (9 L) was slowly added. The mixture was cooled to about 10 °C with continuous stirring for 2 hours. The precipitate was collected by filtration under reduced pressure and dried under reduced pressure at about 50 °C to afford the target product (3R,5S,E)-tert-butyl (3R,5S,E)-7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-enoate (1.22 kg) as white crystals in 88.4% yield.HPLC purity: 98.555%.

References

[1] Patent: US2013/72688, 2013, A1. Location in patent: Paragraph 0060-0062
[2] Patent: US2012/16129, 2012, A1. Location in patent: Page/Page column 13-14
[3] Patent: WO2014/108795, 2014, A2. Location in patent: Page/Page column 19; 20
[4] Patent: JP6231262, 2017, B2. Location in patent: Paragraph 0030-0032

Tert-buthyl Pitavastatin(586966-54-3)Related Product Information

• Pitavastatin lactone dehydration
• Pitavastatin Impurity 2
• Ethyl (E)-7-[4-(4'-fluorophenyl)-2-(cyclopropyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoate
• Pitavastatin Methyl Ester
• PITAVASTATIN LACTONE
• 2-Cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxaldehyde
• 2-Cyclopropyl-3-[(diphenylphosphinyl)methyl]-4-(4-fluorophenyl)quinoline
• (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile
• 2-Cyclopropyl-4-(4-fluorophenyl)-quinolyl-3-methanol
• Pitavastatin calcium
• [2-Cyclopropyl-4-(4-fluorophenyl)-quinolin-3-ylmethyl]-triphenyl-phosphonium bromido
• tert-Butyl (4R-cis)-6-formaldehydel-2,2-dimethyl-1,3-dioxane-4-acetate
• (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl-2-propenal
• (3S,5S,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic Acid CalciuM Salt
• (3S,5R,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid
• (3S,5R,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic Acid CalciuM Salt
• (4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester
• 3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline