Water → Atorvastatin calcium

HRID 901313Notes

Reaction equation

HRID 901313 reaction equation
C([O:5][C:6](=[O:52])[CH2:7][CH:8]1[CH2:13][CH:12]([CH2:14][CH2:15][N:16]2[CH:20]([CH:21]([CH3:23])[CH3:22])[CH:19]([C:24](=[O:32])[NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:18]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:17]2[C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=2)[O:11]B(C2C=CC=CC=2)[O:9]1)(C)(C)C.O.[O-2].[Ca+2:55]>C1COCC1>[CH3:23][CH:21]([C:20]1[N:16]([CH2:15][CH2:14][C@@H:12]([OH:11])[CH2:13][C@@H:8]([OH:9])[CH2:7][C:6]([O-:52])=[O:5])[C:17]([C:39]2[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=2)=[C:18]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:19]=1[C:24]([NH:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:32])[CH3:22].[CH3:23][CH:21]([C:20]1[N:16]([CH2:15][CH2:14][C@@H:12]([OH:11])[CH2:13][C@@H:8]([OH:9])[CH2:7][C:6]([O-:52])=[O:5])[C:17]([C:39]2[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=2)=[C:18]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:19]=1[C:24]([NH:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:32])[CH3:22].[Ca+2:55]

Participants

5

Reactant 3

HCID 962WaterHCID 6850728CalciumoxideHCID 58626912HCID 58626912, compound

Product 1

HCID 60822Atorvastatin calcium

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

A mixture of (6-{2-[2-(4-Fluoro-phenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrolidin-1-yl]-ethyl}-2-phenyl-[1,3,2]dioxaborinan-4-yl)-acetic acid tert-butyl ester (50 g, 0.07 mol), water (2 L), THF (2 L) and calcium oxide (50 g, 0.9 mol) was stirred at 50-60° C. for 8 hours. After filtering the reaction mixture, the resulting clear filtrate was concentrated to about 1.5 L and washed with methyl tert-butyl ether (500 ml). The aqueous layer was evaporated and solid obtained was dissolved in THF (500 ml). The solution was filtered and concentrated to yield atorvastatin calcium.

Workup

  1. filtrationAfter filtering the reaction mixture
  2. concentrationthe resulting clear filtrate was concentrated to about 1.5 L
  3. washwashed with methyl tert-butyl ether (500 ml)
  4. customThe aqueous layer was evaporated
  5. customsolid obtained
  6. filtrationThe solution was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e39fad977ef8444a8903247b94a126ab
Source dataset
uspto-grants-2008_04
Patent number
US07361772B2

Reaction notes

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