Hydrochloric Acid → HCID 117760154, compound

HRID 1049508Notes

Reaction equation

HRID 1049508 reaction equation
[C:1]([C:5]1[O:9][C:8]([C:10]2[CH:15]=[C:14]([O:16][CH2:17][C:18]3[CH:19]=[C:20]([CH:24]([CH:31]4[CH2:33][CH2:32]4)[CH2:25][C:26]([O:28]CC)=[O:27])[CH:21]=[CH:22][CH:23]=3)[CH:13]=[CH:12][C:11]=2[C:34]2[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:35]=2[F:42])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O.Cl>CO.C1COCC1>[C:1]([C:5]1[O:9][C:8]([C:10]2[CH:15]=[C:14]([O:16][CH2:17][C:18]3[CH:19]=[C:20]([CH:24]([CH:31]4[CH2:33][CH2:32]4)[CH2:25][C:26]([OH:28])=[O:27])[CH:21]=[CH:22][CH:23]=3)[CH:13]=[CH:12][C:11]=2[C:34]2[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:35]=2[F:42])=[N:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 117759564HCID 117759564, compound

Product 1

HCID 117760154HCID 117760154, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(3-(((2-(5-(tert-butyl)-1,3,4-oxadiazol-2-yl)-2′-fluoro-5′-methoxy-[1,1′-biphenyl]-4-yl)oxy)methyl)phenyl)-3-cyclopropylpropanoate (115 mg) in methanol (1.0 mL) and THF (1.0 mL) was added 1N aqueous sodium hydroxide solution (0.60 mL), and the mixture was stirred at room temperature for 2 hr. Water and 1N hydrochloric acid were added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (62 mg) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-65e03ea309884f2e814ce0e21332a9c2
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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