Sulfuric Acid → Pitavastatin lactone

HRID 445947

Reaction equation

HRID 445947 reaction equation
[CH:1]1([C:4]2[C:13](/[CH:14]=[CH:15]/[C@H:16]3[O:21]C(C)(C)[O:19][C@@H:18]([CH2:24][C:25](N(OC)C)=[O:26])[CH2:17]3)=[C:12]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:3][CH2:2]1.S(=O)(=O)(O)O>C(#N)C>[CH:1]1([C:4]2[C:13](/[CH:14]=[CH:15]/[C@H:16]3[O:21][C:25](=[O:26])[CH2:24][C@H:18]([OH:19])[CH2:17]3)=[C:12]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86761897E-(6-{2-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]vinyl}-[(4R,6S)-2,2-dimethyl-[1,3]dioxan-4-yl])-N-methoxy-N-methyl-acetamide

Product 1

HCID 9801294Pitavastatin lactoneYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

E-(6-{2-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]vinyl}-[(4R,6S)-2,2-dimethyl-[1,3]dioxan-4-yl])-N-methoxy-N-methyl-acetamide (3.0 g), acetonitrile (50.0 mL), and sulfuric acid (0.3 mL) were added to a reactor. The reaction mixture was stirred at 50˜60° C. for 5 hours and then concentrated under reduced pressure. Ethyl acetate (50.0 mL) and water (50.0 mL) were added to the resulting residue. The separated organic layer was dried under reduced pressure to obtain 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 (1.2 g, yield 50%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionEthyl acetate (50.0 mL) and water (50.0 mL) were added to the resulting residue
  3. customThe separated organic layer was dried under reduced pressure

Sources & evidence

ORD record
ord-d5ff2873e59945d4b69ddd42d14e0349
Source dataset
uspto-grants-2013_07
Patent number
US08476432B2

Linked notes

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