Hydrofluoric Acid → HCID 86751393, compound

HRID 1600350Notes

Reaction equation

HRID 1600350 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

3

Reactant 2

HCID 14917Hydrofluoric AcidHCID 86751394HCID 86751394, compound

Product 1

HCID 86751393HCID 86751393, compound

Procedure

The methyl (3R,6E)-3[(tert-butyldimethylsilyl)oxy]-7-(2,4-dichlorophenyl)-5-oxo-6-heptenoate is treated with hydrogen fluoride to remove the tert-butyldimethylsilyl group so as to give methyl (3R,6E)-7-(2,4-dichlorophenyl)-5-oxo-3-hydroxy-6-heptenoate, which is in turn converted into methyl (3R,5S,6E)-7-(2,4-dichlorophenyl)-3,5-dihydroxy-6-heptenoate by the Syn reduction using diethylmethoxyborane and sodium borohydride, in the manner described in Japanese Patent Provisional Publication H5(1993)-178841. Thus obtained methyl (3R,5S, 6E)-7-(2,4-dichlorophenyl)-3,5-dihydroxy-6-heptenoate 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 the (+)-trans-(E)-6-[2-(2,4-dichlorophenyl)ethenyl]-3,4,5,6-tetrahydroxy-2H-pyran-2-one having the HMG-Co A reductase preventive action.

Workup

  1. customto remove the tert-butyldimethylsilyl group so as

Sources & evidence

ORD record
ord-c5df37bee4d64c989b515b7d7ee703a1
Source dataset
uspto-grants-1998_04
Patent number
US05744604

Reaction notes

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