HCID 15229008, compound → p-Hydroxyatorvastatin lactone

HRID 1770189Notes

Reaction equation

HRID 1770189 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH2:14][C@@H:15]3[CH2:20][C@@H:19]([OH:21])[CH2:18][C:17](=[O:22])[O:16]3)[C:11]([CH:23]([CH3:25])[CH3:24])=[C:10]([C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([O:35]CC4C=CC=CC=4)=[CH:31][CH:30]=3)=[O:27])[C:9]=2[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:4][CH:3]=1>[Pd].C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH2:13][CH2:14][C@@H:15]3[CH2:20][C@@H:19]([OH:21])[CH2:18][C:17](=[O:22])[O:16]3)[C:11]([CH:23]([CH3:24])[CH3:25])=[C:10]([C:26]([NH:28][C:29]3[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=3)=[O:27])[C:9]=2[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 15229008HCID 15229008, compound

Product 1

HCID 9937602p-Hydroxyatorvastatin lactoneYield 6,887.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
24 °C

Procedure

A mixture of 4.7 g (7.26 mmol) of the benzyl ether from Step D above and 1.0 g of 10% palladium on carbon in 300 mL of ethyl acetate was stirred at 24° C. under hydrogen for 3 days. The mixture was filtered to remove the catalyst, and the solvent was removed by evaporation under reduced pressure to give an oil. The oil was crystallized from fresh ethyl acetate to provide 3.5 g of (2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N-(4-hydroxyphenyl)-4-phenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)-ethyl]-1H-pyrrole-3-carboxamide (containing 0.5 mol of ethyl acetate), mp 130°-133° C.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. customthe solvent was removed by evaporation under reduced pressure
  4. customto give an oil
  5. customThe oil was crystallized from fresh ethyl acetate

Sources & evidence

ORD record
ord-d0ad4f242caf4e5a98051b0aaa659231
Source dataset
uspto-grants-1995_01
Patent number
US05385929

Reaction notes

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