Diethylamine → Diethylamine

HRID 71013

Reaction equation

HRID 71013 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[CH3:6][CH:7]([C:9]1[N:13]([CH2:14][CH2:15][C@@H:16]([OH:24])[CH2:17][C@@H:18]([OH:23])[CH2:19][C:20]([OH:22])=[O:21])[C:12]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[C:11]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:10]=1[C:38]([NH:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)=[O:39])[CH3:8]>C(#N)C>[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[CH3:8][CH:7]([C:9]1[N:13]([CH2:14][CH2:15][C@@H:16]([OH:24])[CH2:17][C@@H:18]([OH:23])[CH2:19][C:20]([OH:22])=[O:21])[C:12]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[C:11]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:10]=1[C:38]([NH:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:39])[CH3:6].[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 60823Atorvastatin3×

Product 2

HCID 8021DiethylamineHCID 11556397Atorvastatin diethylamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

The diethylamine salt of atorvastatin (Form A) was synthesized by preparing a stock solution of the free acid of atorvastatin (U.S. Pat. No. 5,273,995) in acetonitrile (1 g in 40 mL of ACN). A solution of diethylamine was prepared by dissolving 132.33 mg (1.0 equivalents) in acetonitrile (20 mL). The stock solution of atorvastatin free acid was added to the counterion solution with stirring. Over time, an additional 40 mL of acetonitrile was added to prevent the formation of a gel. After 5 days of stirring at ambient temperature, the solids were isolated by vacuum filtration using a Buchner funnel fitted with a paper filter (#2 Whatman). The solids were rinsed with acetonitrile (75 mL), and placed in a 25° C. oven under nitrogen to dry overnight to afford atorvastatin diethylamine Form A.

Workup

  1. stirringAfter 5 days of stirring at ambient temperature
  2. customthe solids were isolated by vacuum filtration
  3. customfitted with a paper
  4. filtrationfilter (#2 Whatman)
  5. washThe solids were rinsed with acetonitrile (75 mL)
  6. customplaced in a 25° C.
  7. customto dry overnight

Sources & evidence

ORD record
ord-36de434695f84921a6b84d658f29faa3
Source dataset
uspto-grants-2014_09
Patent number
US08822703B2

Linked notes

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