ChemicalBook--->CAS DataBase List--->586966-54-3

586966-54-3

586966-54-3 Structure

586966-54-3 Structure
IdentificationBack Directory
[Name]

Tert-buthyl Pitavastatin
[CAS]

586966-54-3
[Synonyms]

Tert-butyl Pitavastatin
Tert-buthyl Pitavastatin
Pitavastatin t-Butyl Ester
Pitavastatin tert-Butyl Ester
pitavastatin-defluorination impurity
(3R,5S,E)-tert-butyl 7-(2-cyclopropyl-4-
5-dihydroxy-6-heptenoic acid tert-butyl ester
Pitavastatin Impurity 11(Pitavastatin t-Butyl Ester)
6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3
(3R,5S,E)-tert-Butyl 7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-eno
(3R,5S,6E)7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-3,5-dihydrosy-6-heptaneacid,ethylester
tert-butyl (3R,5S,E)-7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-enoate
7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid tert-butyl ester
(3R,5S,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl) quinolin-3-yl]-3,5-dihydroxyhept-6-enoic acid t-butyl ester
(3R,5S,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid tert-butyl ester
6-Heptenoic acid, 7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-, 1,1-dimethylethyl ester, (3R,5S,6E)-
[EINECS(EC#)]

1308068-626-2
[Molecular Formula]

C29H32FNO4
[MDL Number]

MFCD12755990
[MOL File]

586966-54-3.mol
[Molecular Weight]

477.57
Chemical PropertiesBack Directory
[Boiling point ]

674.5±55.0 °C(Predicted)
[density ]

1.235±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,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
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Uses]

tert-Butyl Pitavastatin is used to prepare hemicalcium salt.
[Synthesis]

(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

147489-06-3

Tert-buthyl Pitavastatin

586966-54-3

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
Spectrum DetailBack Directory
[Spectrum Detail]

Tert-buthyl Pitavastatin(586966-54-3)1HNMR
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