Hydrochloric Acid → HCID 23157650, compound

HRID 508098Notes

Reaction equation

HRID 508098 reaction equation
[CH2:1]([S:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH2:16][CH2:17][CH:18]3[N:23]([S:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[N+:47]([O-:49])=[O:48])(=[O:40])=[O:39])[C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])=[C:26]([F:37])[CH:25]=2)=[C:9]([CH3:50])[CH:8]=1)[CH3:2].C(O)C.[OH-].[Na+].Cl>O1CCCC1>[CH2:1]([S:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH2:16][CH2:17][CH:18]3[N:23]([S:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[N+:47]([O-:49])=[O:48])(=[O:40])=[O:39])[C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[C:26]([F:37])[CH:25]=2)=[C:9]([CH3:50])[CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 23157179ethyl 3-(4-{(4-{4-[2-(ethylthio)ethoxy]-2,6-dimethylphenyl}-2,3-dihydro-1H-inden-1-yl)[(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate

Product 1

HCID 23157650HCID 23157650, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 3-(4-{(4-{4-[2-(ethylthio)ethoxy]-2,6-dimethylphenyl}-2,3-dihydro-1H-inden-1-yl)[(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate (1.06 g, 1.47 mmol), ethanol (5 mL) and tetrahydrofuran (5 mL) was added 1 N aqueous sodium hydroxide solution (2.94 mL, 2.94 mmol), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was neutralized with 1 N hydrochloric acid, and concentrated under reduced pressure to evaporate the organic solvent. The residue was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (20%-100% ethyl acetate/hexane) to give the title compound (0.804 g, yield 79%) as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto evaporate the organic solvent
  3. extractionThe residue was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (20%-100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c9519599e1a14341ab64497795d0c286
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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