Hydrochloric Acid → HCID 59634062, compound

HRID 1615075Notes

Reaction equation

HRID 1615075 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:11][N:10]([C:12]([C:14]3[CH:19]=[C:18]([O:20][CH2:21][CH2:22][O:23]C4CCCCO4)[CH:17]=[CH:16][N:15]=3)=[O:13])[CH2:9]2)=[CH:4][C:3]=1[O:30][CH3:31].Cl.[OH-].[Na+].C([O-])(O)=O.[Na+]>O1CCCC1>[OH:23][CH2:22][CH2:21][O:20][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([C:12]([N:10]2[CH2:9][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:30][CH3:31])[CH:4]=3)[CH2:11]2)=[O:13])[CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 59633970HCID 59633970, compound2×

Product 1

HCID 59634062HCID 59634062, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the crude [3-(4-hydroxy-3-methoxyphenyl)azetidin-1-yl]-{4-[2-(tetrahydropyran-2-yloxy)ethoxy]pyridin-2-yl}-methanone prepared in (1) in THF (5.0 mL) was added 1 N hydrochloric acid (5.0 mL). The reaction mixture was stirred at RT for 13 hr. To the reaction mixture were added aqueous 1 N NaOH and saturated aqueous NaHCO3 and then the mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: chloroform/methanol=9/1) to give the title compound (0.70 g, 75%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel chromatography (Developing solvent: chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-bb106d0763e1462c809096bfb419dede
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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