Hydrochloric Acid → HCID 16048403, compound

HRID 1691535Notes

Reaction equation

HRID 1691535 reaction equation
[O:1]=[S:2]1(=[O:38])[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][O:23][C:24]4[CH:29]=[CH:28][C:27]([CH:30]5[CH2:32][CH:31]5[C:33]([O:35]C)=[O:34])=[CH:26][CH:25]=4)[CH:17]=3)=[C:11]([CH3:37])[CH:10]=2)[CH2:4][CH2:3]1.[OH-].[Na+].Cl>CO.O1CCCC1>[O:1]=[S:2]1(=[O:38])[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][O:23][C:24]4[CH:25]=[CH:26][C:27]([CH:30]5[CH2:32][CH:31]5[C:33]([OH:35])=[O:34])=[CH:28][CH:29]=4)[CH:17]=3)=[C:11]([CH3:37])[CH:10]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59364070HCID 59364070, compound

Product 1

HCID 16048403HCID 16048403, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a mixed solution of methyl 2-[4-({4′-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2′,6′- dimethylbiphenyl-3-yl}methoxy)phenyl]cyclopropanecarboxYlate (0.392 g, 0.733 mmol) in methanol (6 mL) and tetrahydrofuran (12 mL) was added 2 M aqueous sodium hydroxide solution (3 mL), and the mixture was stirred at 50° C. for 2 hr. 1 M Hydrochloric acid (10 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=50:50-90:10) and recrystallized from ethyl acetate-hexane to give the title compound (0.129 g, yield 34%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=50:50-90:10)
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f69b050fadc64d5db2ee22442f1832cb
Source dataset
uspto-grants-2012_04
Patent number
US08153694B2

Reaction notes

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