Hydrochloric Acid → HCID 117760160, compound

HRID 1049565Notes

Reaction equation

HRID 1049565 reaction equation
P([O-])(O)(O)=O.[Na+].Cl([O-])=[O:8].[Na+].CC(=CC)C.[F:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:34]=[C:35]([CH:39]([CH2:46][CH:47]=[O:48])[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:36]=[CH:37][CH:38]=2)=[CH:27][C:26]=1[CH2:49][C:50]([CH3:53])([CH3:52])[CH3:51].Cl>O.CC(O)(C)C>[CH2:44]([O:43][C:41](=[O:42])[CH2:40][CH:39]([C:35]1[CH:36]=[CH:37][CH:38]=[C:33]([CH2:32][O:31][C:28]2[CH:29]=[CH:30][C:25]([C:18]3[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:17]=3[F:16])=[C:26]([CH2:49][C:50]([CH3:52])([CH3:51])[CH3:53])[CH:27]=2)[CH:34]=1)[CH2:46][C:47]([OH:8])=[O:48])[CH3:45]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 117759767HCID 117759767, compound

Product 1

HCID 117760160HCID 117760160, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

Sodium dihydrogenphosphate (230 mg), sodium chlorite (174 mg) and 2-methyl-2-butene (339 μL) were successively added to a mixture of ethyl 3-(3-(((2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-yl)oxy)methyl)phenyl)-5-oxopentanoate, 2-methyl-2-propanol (4 mL) and water (1 mL), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added 1N hydrochloric acid at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (269 mg) as a colorless amorphous solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2315c2465c9d499cb69f1a152093cae7
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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