Hydrochloric Acid → HCID 23157272, compound

HRID 508056Notes

Reaction equation

HRID 508056 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][C:29]([F:36])([F:35])[C:30]([O:32]CC)=[O:31])=[CH:24][CH:23]=3)[CH:15]=2)=[C:9]([CH3:37])[CH:8]=1)[CH3:2].O1CCCC1.O.[OH-].[Li+].Cl>O.C(O)C>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH3:37])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]3[CH:23]=[CH:24][C:25]([CH2:28][C:29]([F:35])([F:36])[C:30]([OH:32])=[O:31])=[CH:26][CH:27]=3)[CH:15]=2)=[C:11]([CH3:13])[CH:12]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 23157621HCID 23157621, compound

Product 1

HCID 23157272HCID 23157272, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 3-[4-({[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methyl}amino)phenyl]-2,2-difluoropropanoate (665 mg, 1.30 mmol), tetrahydrofuran (15 mL), ethanol (10 mL), water (10 mL) and lithium hydroxide monohydrate (162 mg, 3.89 mmol) was stirred at room temperature for 3 hr. The reaction mixture was neutralized with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (20%-100% ethyl acetate/hexane), and the residue was recrystallized from ethyl acetate-hexane to give the title compound (415 mg, yield 66%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (20%-100% ethyl acetate/hexane)
  6. customthe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a1f26e4881554ef0bae225503ae542da
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

Loading…