Ethyl Acetate → Atorvastatin calcium propylene glycol solvate

HRID 1173811Notes

Reaction equation

HRID 1173811 reaction equation
[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]([O-: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].[CH3:42][CH:43]([C:45]1[N:49]([CH2:50][CH2:51][C@@H:52]([OH:60])[CH2:53][C@@H:54]([OH:59])[CH2:55][C:56]([O-:58])=[O:57])[C:48]([C:61]2[CH:62]=[CH:63][C:64]([F:67])=[CH:65][CH:66]=2)=[C:47]([C:68]2[CH:69]=[CH:70][CH:71]=[CH:72][CH:73]=2)[C:46]=1[C:74]([NH:76][C:77]1[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=1)=[O:75])[CH3:44].[Ca+2:83].C(OCC)(=[O:86])C>C(O)C(O)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]([O-: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])[CH3:1].[CH3:44][CH:43]([C:45]1[N:49]([CH2:50][CH2:51][C@@H:52]([OH:60])[CH2:53][C@@H:54]([OH:59])[CH2:55][C:56]([O-:58])=[O:57])[C:48]([C:61]2[CH:62]=[CH:63][C:64]([F:67])=[CH:65][CH:66]=2)=[C:47]([C:68]2[CH:69]=[CH:70][CH:71]=[CH:72][CH:73]=2)[C:46]=1[C:74]([NH:76][C:77]1[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=1)=[O:75])[CH3:42].[CH3:15][CH:14]([OH:86])[CH2:13][OH:18].[Ca+2:83]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 60822Atorvastatin calcium

Product 1

HCID 51039411Atorvastatin calcium propylene glycol solvate

Reagents, catalysts & solvents 1

HCID 1030Propylene GlycolSolvent

Conditions

Temperature
57.5 °C

Procedure

Atorvastatin calcium (5 g) was dissolved in racemic propylene glycol followed by the addition of 7 parts of ethyl acetate. The resulting mixture was warmed to 55-60° C. and stirred for 8-10 hours to afford a white suspension. The suspension was cooled to 20-25° C. and filtered to provide 3.3 g of atorvastatin calcium propylene glycol solvate after drying under vacuum at 50-60° C. Propylene glycol content: 6% by NMR.

Workup

  1. customto afford a white suspension
  2. temperatureThe suspension was cooled to 20-25° C.
  3. filtrationfiltered

Sources & evidence

ORD record
ord-9e753dbeaeb14b8fa2f65d03ab272d16
Source dataset
uspto-grants-2010_11
Patent number
US07834195B2

Reaction notes

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