Hydrochloric Acid → Pitavastatin

HRID 445950

Reaktionsgleichung

Reaktionsgleichung von HRID 445950
C(NC(C)C)(C)C.[CH:8]1([C:11]2[C:20](/[CH:21]=[CH:22]/[C@@H:23]([OH:31])[CH2:24][C@@H:25]([OH:30])[CH2:26][C:27]([OH:29])=[O:28])=[C:19]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH2:10][CH2:9]1.Cl.[OH-].[Na+].O.O.[Cl-].[Ca+2].[Cl-]>O.C(OCC)(=O)C>[CH:8]1([C:11]2[C:20](/[CH:21]=[CH:22]/[C@@H:23]([OH:31])[CH2:24][C@@H:25]([OH:30])[CH2:26][C:27]([OH:29])=[O:28])=[C:19]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH2:10][CH2:9]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 6093260Calcium chloride, dihydrateHCID 60150999HCID 60150999, Verbindung

Produkt 1

HCID 5282452PitavastatinAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy hept-6-enoic acid diisopropylamine salt (10.0 g) in a mixed solvent of ethyl acetate (100.0 mL) and water (100.0 mL) was cooled to 0˜5° C. The pH of the reaction mixture was adjusted to 3.0˜4.0 using 1N hydrochloric acid solution. Water (40.0 mL) was added to the separated organic layer, the pH of which was then adjusted to 9.0˜11.5 using 1N sodium hydroxide solution. Calcium chloride dihydrate (2.8 g) was added to the separated water layer. The reaction mixture was stirred at 20˜25° C. for 2 hours and then filtered under reduced pressure. The resulting white solid was dried to obtain (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy hept-6-enoic acid 1/2 calcium salt (6.9 g, yield 90%).

Aufarbeitung

  1. filtrationfiltered under reduced pressure
  2. customThe resulting white solid was dried

Quellen und Nachweise

ORD-Eintrag
ord-b4cfd5bab0f64a8cbc35a95f638e6bdc
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476432B2

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