Sulfuric Acid → Rosuvastatin Lactone

HRID 445940

Reaction equation

HRID 445940 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](C)([CH3:28])[O:25][C@@H:24](CC(N(OC)C)=O)[CH2:23]2)=[C:9]([CH:37]([CH3:39])[CH3:38])[N:8]=1)[S:3]([CH3:6])(=[O:5])=[O:4].S(=O)(=O)(O)[OH:41]>C(#N)C>[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:41])[CH2:28][C@H:24]([OH:25])[CH2:23]2)=[C:9]([CH:37]([CH3:39])[CH3:38])[N:8]=1)[S:3]([CH3:6])(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86681509E-(6-{2-[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-yl]vinyl}-[(4R,6S)-2,2-dimethyl-[1,3]dioxan-4-yl])-N-methoxy-N-methyl-acetamide

Product 1

HCID 29918986Rosuvastatin LactoneYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

E-(6-{2-[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-yl]vinyl}-[(4R,6S)-2,2-dimethyl-[1,3]dioxan-4-yl])-N-methoxy-N-methyl-acetamide (5.0 g), acetonitrile (30.0 mL), and sulfuric acid (0.47 mL) were added to a reactor and then the reaction mixture was stirred at 50˜60° C. for 3 hours. The reaction mixture was concentrated under reduced pressure and then ethyl acetate (30.0 mL) and water (30.0 mL) were added thereto. The separated organic layer was dried under reduced pressure to obtain 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 (3.4 g, yield 82%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionethyl acetate (30.0 mL) and water (30.0 mL) were added
  3. customThe separated organic layer was dried under reduced pressure

Sources & evidence

ORD record
ord-1b21f6e633a44c6cac51141123ee2d5b
Source dataset
uspto-grants-2013_07
Patent number
US08476432B2

Linked notes

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