Hydrofluoric Acid → HCID 86751393, compound
Reaction equation
[Si]([O:8][C@H:9]([CH2:15][C:16](=[O:27])/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[Cl:26])[CH2:10][C:11]([O:13][CH3:14])=[O:12])(C(C)(C)C)(C)C.F>>[Cl:26][C:20]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=1/[CH:18]=[CH:17]/[C:16](=[O:27])[CH2:15][C@@H:9]([OH:8])[CH2:10][C:11]([O:13][CH3:14])=[O:12]Participants
Procedure
For instance, methyl (3R,6E)-3-[(tert-butyldimethylsilyl)oxy]-7-(2,4-dichlorophenyl)-5-oxo-6-heptenoate (which is one of the compounds of the formula (1)) is subjected to the tert-butyldimethylsilyl removing step using hydrogen fluoride in the manner as described in Japanese Patent Provisional Publication H5 (1993)-178841, to give methyl (3R,6E)-7-(2,4-dichlorophenyl)-3-hydroxy-5-oxo-6-heptenoate. The obtained ester is then subjected to Syn reduction using diethylmethoxyborane and sodium borohydride (NaBH4), to give methyl (3R,5S,6E)-7-(2,4-dichlorophenyl)-3,5-dihydroxy-6-heptenoate. Subsequently, thus obtained ester is treated with sodium hydroxide and hydrochloric acid in the manner as described in Journal of Medicinal Chemistry, 1985, vol. 28, No. 3, pp. 347-358, to give (+)-trans-(E)-6-[2-(2,4-dichlorophenyl)ethenyl]3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-on which has the 3-hydroxy-3-methylglutaryl Coenzyme A reductase preventive action.
Sources & evidence
- ORD record
- ord-1e8ee0160fa146d2a7a4c07629718e85
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05677455
Reaction notes
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