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Pravastatin → Des(2-methylbutyryl) Pravastatin Sodium Salt

HRID 400133
Notes
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Reaction equation

HRID 400133 reaction equation
C[O-].[Na+:3].[OH:4][C@H:5]([CH2:10][C@H:11]([OH:33])[CH2:12][CH2:13][C@@H:14]1[C@@H:23]2[C:18](=[CH:19][C@@H:20]([OH:31])[CH2:21][C@@H:22]2[O:24]C(=O)[C@@H](C)CC)[CH:17]=[CH:16][C@@H:15]1[CH3:32])[CH2:6][C:7]([O-:9])=[O:8].CC[C@@H](C(O[C@@H]1[C@@H]2[C@@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@@H](C)C=CC2=C[C@@H](O)C1)=O)C>CO>[OH:4][C@H:5]([CH2:10][C@H:11]([OH:33])[CH2:12][CH2:13][C@@H:14]1[C@@H:23]2[C:18](=[CH:19][C@@H:20]([OH:31])[CH2:21][C@@H:22]2[OH:24])[CH:17]=[CH:16][C@@H:15]1[CH3:32])[CH2:6][C:7]([O-:9])=[O:8].[Na+:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 54687PravastatinHCID 10942334Sodium MethoxideHCID 24849132Pravastatin(1-)

Product 1

HCID 23683819Des(2-methylbutyryl) Pravastatin Sodium Salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

50 ml (0.24 mol) of a 28% w/v solution of sodium methoxide in methanol were added to a solution of 100 g (0.31 mol) of (3R,5R)-3,5-dihydroxy-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-[(S)-2-methyl-butyryloxy]-1,2,6,7,8,8a-hexahydro-1-naphthyl]heptanoate (pravastatin: prepared as described in U.S. Pat. No. 4,346,227) in 900 ml of methanol, and the resulting mixture was heated under reflux for 60 hours. At the end of this time, the mixture was cooled to room temperature, and the methanol was then removed from the reaction mixture by distillation under reduced pressure. The resulting residue was washed with 200 ml of hexane and then dried in vacuo to give 120 g of the title compound.

Workup

  1. customprepared
  2. temperatureunder reflux for 60 hours
  3. customthe methanol was then removed from the reaction mixture by distillation under reduced pressure
  4. washThe resulting residue was washed with 200 ml of hexane
  5. customdried in vacuo

Sources & evidence

ORD record
ord-645d3d9f50a44c4abb270c2a6398bd25
Source dataset
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05827855

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes