Calcium Hydroxide → Pitavastatin

HRID 445948

Reaction equation

HRID 445948 reaction equation
[CH:1]1([C:4]2[C:13](/[CH:14]=[CH:15]/[C@H:16]3[O:21][C:20](=[O:22])[CH2:19][C@H:18]([OH:23])[CH2:17]3)=[C:12]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:3][CH2:2]1.[OH-:31].[Ca+2].[OH-]>O>[CH:1]1([C:4]2[C:13](/[CH:14]=[CH:15]/[C@@H:16]([OH:31])[CH2:17][C@@H:18]([OH:23])[CH2:19][C:20]([OH:21])=[O:22])=[C:12]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6093208Calcium HydroxideHCID 9801294Pitavastatin lactone

Product 1

HCID 5282452PitavastatinYield 95.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

E-6-{2-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]vinyl}-(4R,6S)-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one (2.0 g), water (20.0 mL), and calcium hydroxide (0.4 g) were added to a reactor. The reaction mixture was stirred at room temperature for 3 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 (2.0 g, yield 91%).

Workup

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

Sources & evidence

ORD record
ord-b341d70b64414f0984e71e2f924cb205
Source dataset
uspto-grants-2013_07
Patent number
US08476432B2

Linked notes

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