Methanol → Simvastatin

HRID 381710

Reaction equation

HRID 381710 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]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]([CH3:30])[CH2:10]1)=[O:7])([CH3:5])[CH3:4].B([O-])[O-].CO>O>[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]([CH3:30])[CH2:10]1)=[O:7])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 887MethanolHCID 178445512HCID 178445512, compound

Product 1

HCID 54454Simvastatin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Alternatively, III may be agitated in a mixture of water and an organic solvent, preferably methanol, under high dilution conditions to produce simvastatin in its acid form. Simvastatin acid may be isolated by extraction or crystallization and relactonized to produce simvastatin.

Sources & evidence

ORD record
ord-fd52504a35e746cd8b8005092cc39f97
Source dataset
uspto-grants-2001_10
Patent number
US06307066B1

Linked notes

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