Hydrochloric Acid → HCID 12002221, compound

HRID 508110Notes

Reaction equation

HRID 508110 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([O:24][CH2:25][C:26]4([OH:34])[CH2:31][CH2:30][S:29](=[O:33])(=[O:32])[CH2:28][CH2:27]4)=[CH:19][C:18]=3[CH3:35])[C:13]([CH3:16])=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[CH2:36][CH2:37][C:38]([O:40]CC)=[O:39].[OH-].[Na+].Cl>CO.O1CCCC1.[Cl-].[Na+].O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([O:24][CH2:25][C:26]4([OH:34])[CH2:27][CH2:28][S:29](=[O:33])(=[O:32])[CH2:30][CH2:31]4)=[CH:19][C:18]=3[CH3:35])[C:13]([CH3:16])=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[CH2:36][CH2:37][C:38]([OH:40])=[O:39]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59434133HCID 59434133, compound

Product 1

HCID 12002221HCID 12002221, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of ethyl 3-{2-fluoro-4-[({4′-[(4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy]-2′,6,6′-trimethylbiphenyl-3-yl}methyl)amino]phenyl}propanoate (133 mg, 0.22 mmol) in a mixture of methanol (0.5 mL) and tetrahydrofuran (1 mL) was added 1 M aqueous sodium hydroxide solution (0.66 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was neutralized with 1 M hydrochloric acid, and brine was added. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-ethyl acetate) to give the title compound (72.7 mg, yield 58%) as a colorless amorphous powder.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-ethyl acetate)

Sources & evidence

ORD record
ord-888d1a0142bb49c6989af5b8f5de35c3
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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