Hydrochloric Acid → HCID 12002201, compound

HRID 508076Notes

Reaction equation

HRID 508076 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH2:24][C:25]4([OH:33])[CH2:30][CH2:29][S:28](=[O:32])(=[O:31])[CH2:27][CH2:26]4)=[CH:18][C:17]=3[CH3:34])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[CH2:35][CH2:36][C:37]([O:39]CC)=[O:38].CO.[OH-].[Na+].Cl>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH2:24][C:25]4([OH:33])[CH2:26][CH2:27][S:28](=[O:32])(=[O:31])[CH2:29][CH2:30]4)=[CH:18][C:17]=3[CH3:34])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[CH2:35][CH2:36][C:37]([OH:39])=[O:38]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 59434150HCID 59434150, compound

Product 1

HCID 12002201HCID 12002201, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 3-(2-fluoro-4-[({4′-[(4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy]-2′,6′-dimethylbiphenyl-3-yl)methyl)amino]phenyl}propanoate (1.99 g, 3.40 mmol), methanol (24 mL) and tetrahydrofuran (7 mL) was. added 1 M aqueous sodium hydroxide solution (10.2 mL), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was neutralized with 1 M 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 sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1-hexane/ethyl acetate=1/1) and recrystallized from ethyl acetate-hexane to give the title compound (1.47 g, yield 78%) as colorless crystals.

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 sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1-hexane/ethyl acetate=1/1)
  7. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1e7661c0133d48188c55bebe151aae7e
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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