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Calcium Hydroxide → Rosuvastatin

HRID 445942
Notes
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Reaction equation

HRID 445942 reaction equation
[CH3:1][N:2]([C:7]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:10](/[CH:20]=[CH:21]/[C@H:22]2[O:27][C:26](=[O:28])[CH2:25][C@H:24]([OH:29])[CH2:23]2)=[C:9]([CH:30]([CH3:32])[CH3:31])[N:8]=1)[S:3]([CH3:6])(=[O:5])=[O:4].[OH-:33].[Ca+2].[OH-]>O>[CH3:1][N:2]([C:7]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:10](/[CH:20]=[CH:21]/[C@@H:22]([OH:27])[CH2:23][C@@H:24]([OH:29])[CH2:25][C:26]([OH:28])=[O:33])=[C:9]([CH:30]([CH3:31])[CH3:32])[N:8]=1)[S:3]([CH3:6])(=[O:5])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6093208Calcium HydroxideHCID 29918986Rosuvastatin Lactone

Product 1

HCID 446157RosuvastatinYield 98.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

E-6-{2-[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-yl]vinyl}-(4R,6S)-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one (4.0 g), water (20.0 mL), and calcium hydroxide (0.64 g) was 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 E-7-[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxyhept-6-enoic acid 1/2 calcium salt (4.1 g, yield 95%).

Workup

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

Sources & evidence

ORD record
ord-a54ed2d198cc49cb9bce7d3455ccd746
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08476432B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes