Ethyl Acetate → (R)-5-(4-{1-ethyl-1-[4'-(1-hydroxy-1-methyl-ethyl)-2-methyl-biphenyl-4-yl]-propyl}-2-methyl-phenoxy)-4-hydroxy-pentanoic Acid

HRID 546826Notes

Reaction equation

HRID 546826 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([C:21]([C:45]1[CH:58]=[CH:57][C:48]([O:49][CH2:50][C@@H:51]2[O:55][C:54](=[O:56])[CH2:53][CH2:52]2)=[C:47]([CH3:59])[CH:46]=1)([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([CH3:43])([O:38][Si](C)(C)C)[CH3:37])=[CH:32][CH:31]=2)=[C:26]([CH3:44])[CH:25]=1)[CH2:22][CH3:23])[CH3:20].C(OCC)(=[O:62])C>O1CCCC1>[CH2:19]([C:21]([C:45]1[CH:58]=[CH:57][C:48]([O:49][CH2:50][C@H:51]([OH:62])[CH2:52][CH2:53][C:54]([OH:55])=[O:56])=[C:47]([CH3:59])[CH:46]=1)([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([OH:38])([CH3:37])[CH3:43])=[CH:32][CH:31]=2)=[C:26]([CH3:44])[CH:25]=1)[CH2:22][CH3:23])[CH3:20]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 57708923(R)-5-(4-{1-ethyl-1-[2-methyl-4'-(1-methyl-1-trimethylsilanyloxy-ethyl)-biphenyl-4-yl]-propyl}-2-methyl-phenoxymethyl)-dihydro-furan-2-one

Product 1

HCID 57709071(R)-5-(4-{1-ethyl-1-[4'-(1-hydroxy-1-methyl-ethyl)-2-methyl-biphenyl-4-yl]-propyl}-2-methyl-phenoxy)-4-hydroxy-pentanoic AcidYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
75 °C

Procedure

A 1.0 M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (0.1 mL, 0.1 mmol) was added to a solution of (R)-5-(4-{1-ethyl-1-[2-methyl-4′-(1-methyl-1-trimethylsilanyloxy-ethyl)-biphenyl-4-yl]-propyl}-2-methyl-phenoxymethyl)-dihydro-furan-2-one (Example 15-(4); 16 mg, 0.028 mmol) in tetrahydrofuran (0.1 mL) at room temperature, and the mixture was stirred at 75° C. for two hours. Ethyl acetate was added to the reaction solution. The organic layer was washed with a potassium bisulfate aqueous solution and brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (dichloromethane/methanol=10/1, developed three times) to give the title compound (11.3 mg, 78%).

Workup

  1. washThe organic layer was washed with a potassium bisulfate aqueous solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel chromatography (dichloromethane/methanol=10/1, developed three times)

Sources & evidence

ORD record
ord-3f045fa57b0041059493c17c9e219f73
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

Loading…