Water → Atorvastatin

HRID 254877

Reaktionsgleichung

Reaktionsgleichung von HRID 254877
[CH3:1][CH:2]([C:4]1[N:8]([CH2:9][CH2:10][C@@H:11]([OH:19])[CH2:12][C@@H:13]([OH:18])[CH2:14][C:15]([OH:17])=[O:16])[C:7]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[C:6]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:5]=1[C:33]([NH:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:34])[CH3:3].[OH-].[NH4+:43].O>C(#N)C>[CH3:3][CH:2]([C:4]1[N:8]([CH2:9][CH2:10][C@@H:11]([OH:19])[CH2:12][C@@H:13]([OH:18])[CH2:14][C:15]([OH:17])=[O:16])[C:7]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:6]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:5]=1[C:33]([NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:34])[CH3:1].[NH4+:43].[F:26][C:23]1[CH:22]=[CH:21][C:20]([C:7]2[N:8]([CH2:9][CH2:10][CH:11]([OH:19])[CH2:12][CH:13]([OH:18])[CH2:14][C:15]([O-:17])=[O:16])[C:4]([CH:2]([CH3:3])[CH3:1])=[C:5]([C:33]([NH:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[O:34])[C:6]=2[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:25][CH:24]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 60823Atorvastatin2×

Produkt 2

HCID 60823AtorvastatinHCID 730592022-(4-Fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid, ammonium salt

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel3×

Versuchsvorschrift

The ammonium salt of atorvastatin was synthesized by preparing a stock solution of the free acid of atorvastatin (U.S. Pat. No. 5,273,995) in acetonitrile (ACN) (0.634 g in 25 mL of ACN). A solution was prepared by dissolving 12.04 mg of ammonium hydroxide (1.0 equivalents) in acetonitrile (0.5 mL). The stock solution of atorvastatin free acid (2.24 mL) was added to the counterion solution with stirring. If a gel formed, additional acetonitrile and water was added as necessary. After 2 days of stirring at ambient temperature, the solids were isolated by vacuum filtration using a 0.45 μm nylon 66 membrane filter. The solids were rinsed with acetonitrile and air dried at ambient conditions to afford atorvastatin ammonium.

Aufarbeitung

  1. customA solution was prepared
  2. customIf a gel formed
  3. stirringAfter 2 days of stirring at ambient temperature
  4. customthe solids were isolated by vacuum filtration
  5. filtrationfilter
  6. washThe solids were rinsed with acetonitrile and air
  7. customdried at ambient conditions

Quellen und Nachweise

ORD-Eintrag
ord-3b13ba42754f453e9d9c624436c240b0
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875731B2

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