Sodium Hydroxide → Sodium 7-[4-(4-fluorophenyl)-2-[(methanesulfonyl)(methyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate

HRID 222522Notes

Reaction equation

HRID 222522 reaction equation
[CH3:1][CH:2]([C:4]1[C:9](/[CH:10]=[CH:11]/[C@@H:12]([OH:24])[CH2:13][C@@H:14]([OH:23])[CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])=[C:8]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[N:7]=[C:6]([N:32]([S:34]([CH3:37])(=[O:36])=[O:35])[CH3:33])[N:5]=1)[CH3:3].[OH-].[Na+:39]>C1COCC1.O>[CH3:3][CH:2]([C:4]1[C:9]([CH:10]=[CH:11][CH:12]([OH:24])[CH2:13][CH:14]([OH:23])[CH2:15][C:16]([O-:18])=[O:17])=[C:8]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[N:7]=[C:6]([N:32]([S:34]([CH3:37])(=[O:36])=[O:35])[CH3:33])[N:5]=1)[CH3:1].[Na+:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 114782101,1-Dimethylethyl (3R,5S,6E)-7-(4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinyl)-3,5-dihydroxy-6-heptenoate

Product 1

HCID 53394918Sodium 7-[4-(4-fluorophenyl)-2-[(methanesulfonyl)(methyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoateYield 100%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
30 °C

Procedure

Rosuvastatin tert-butyl ester (3.0 g, 5.6 mmol) is dissolved in 25 mL of a 4:1 mixture of THF/water. The clear solution is warmed to 30° C. and 8.0 M NaOH (0.75 mL, 6.0 mmol) was added portionwise. The reaction mixture is stirred at 30° C. for 2 hours giving a clear yellow solution. Then THF is removed completely under the reduced pressure (20 mbar) at 40° C. The remaining aqueous solution is diluted with water to 25 mL and washed with AcOEt (2×10 mL). After separation from the organic layer aqueous phase is distilled under the reduced pressure (20 mbar) at 40° C. to completely remove the dissolved AcOEt. The remaining clear solution of sodium rosuvastatinate is diluted with water to 25 mL and liophylized to afford 2.81 g (100%) of rosuvastatin sodium salt as white powder.

Workup

  1. customgiving a clear yellow solution
  2. customThen THF is removed completely under the reduced pressure (20 mbar) at 40° C
  3. additionThe remaining aqueous solution is diluted with water to 25 mL
  4. washwashed with AcOEt (2×10 mL)
  5. customAfter separation from the organic layer aqueous phase
  6. distillationis distilled under the reduced pressure (20 mbar) at 40° C.
  7. customto completely remove the dissolved AcOEt
  8. additionThe remaining clear solution of sodium rosuvastatinate is diluted with water to 25 mL

Sources & evidence

ORD record
ord-621d485bd6014291810bba4a6f8c0cae
Source dataset
uspto-grants-2012_06
Patent number
US08207333B2

Reaction notes

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