Hydrochloric Acid → HCID 117759672, compound

HRID 1049539Notes

Reaction equation

HRID 1049539 reaction equation
[C:1]([C:5]1[S: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[S: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 117759755HCID 117759755, compound

Product 1

HCID 117759672HCID 117759672, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(3-(((2-(5-(tert-butyl)-1,3,4-thiadiazol-2-yl)-2′-fluoro-5′-methoxy-[1,1′-biphenyl]-4-yl)oxy)methyl)phenyl)-3-cyclopropylpropanoate (129 mg) in methanol (1.5 mL) and THF (1.5 mL) was added 1N aqueous sodium hydroxide solution (0.66 mL), and the mixture was stirred at room temperature for 9 hr. Water and hydrochloric acid were added, and the reaction 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 (122 mg) as a colorless oil.

Workup

  1. extractionthe reaction 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-8bef33d49b694840aec1b60ed2c268db
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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