Sulfuric acid magnesium salt (1:1) → Simvastatin

HRID 1625171Notes

Reaction equation

HRID 1625171 reaction equation
[CH3:1][CH2:2][C:3]([C:6]([O:8][C@@H:9]1[C@@H:14]2[C@@H:15]([CH2:20][CH2:21][C@@H:22](O)[CH2:23][C@@H:24]([OH:29])[CH2:25][C:26]([O-:28])=[O:27])[C@@H:16]([CH3:19])[CH:17]=[CH:18][C:13]2=[CH:12][C@H:11]([CH3:31])[CH2:10]1)=O)([CH3:5])[CH3:4].[NH4+].[OH2:33].C1(C)C=CC(S(O)(=O)=O)=CC=1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)(Cl)Cl>[CH3:1][CH2:2][C:3]([C:6]([O:8][C@@H:9]1[C@@H:14]2[C@@H:15]([CH2:20][CH2:21][C@H:22]3[O:28][C:26](=[O:27])[CH2:25][C@H:24]([OH:29])[CH2:23]3)[C@@H:16]([CH3:19])[CH:17]=[CH:18][C:13]2=[CH:12][C@H:11]([CH3:31])[CH2:10]1)=[O:33])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 521998p-Toluenesulfonic acid monohydrateHCID 10961424Simvastatin ammonium salt

Product 1

HCID 54454SimvastatinYield 86.93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

100 g of simvastatin ammonium salt, 800 ml of chloroform, 43.2 g of p-toluenesulfonic acid monohydrate, and 20 g of anhydrous magnesium sulfate were added to a 1 L reaction flask, and the reaction mixture were allowed to stir at 15˜20° C. until the end of reaction. A TLC monitoring was carried out at the end of the reaction. Subsequently, simvastatin 80.2 g was obtained by the same procedure as described in example 3 with a yield of 86.93%, in which a content of simvastatin was 99.48%, and a content of a dimmer thereof was 0.14%.

Workup

  1. customA TLC monitoring was carried out at the end of the reaction

Sources & evidence

ORD record
ord-1c34675c0ec141239316cad1d7a95fe1
Source dataset
uspto-grants-2014_07
Patent number
US08779167B2

Reaction notes

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