Nitric Acid → Rosuvastatin Lactone

HRID 445941

Reaktionsgleichung

Reaktionsgleichung von HRID 445941
[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].[N+]([O-])(O)=[O: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]

Komponenten

4

Edukt 2

HCID 944Nitric 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

Produkt 1

HCID 29918986Rosuvastatin LactoneAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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 (4.0 g), acetonitrile (25.0 mL), and nitric acid (0.49 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 (25.0 mL) and water (25.0 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 (1.9 g, yield 58%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionethyl acetate (25.0 mL) and water (25.0 mL) were added
  3. customThe separated organic layer was dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e2873b87826c4a31ae23cd30d5f18f6c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476432B2

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