Hydrochloric Acid → HCID 59434134, compound

HRID 508114Notes

Reaction equation

HRID 508114 reaction equation
[C:1]([NH:4][C:5]1[C:10]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([O:18][CH2:19][C:20]3([OH:28])[CH2:25][CH2:24][S:23](=[O:27])(=[O:26])[CH2:22][CH2:21]3)=[CH:13][C:12]=2[CH3:29])=[CH:9][C:8]([CH2:30][NH:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][C:40]([O:42]CC)=[O:41])=[C:34]([F:45])[CH:33]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>CO.O1CCCC1.[Cl-].[Na+].O>[C:1]([NH:4][C:5]1[C:10]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([O:18][CH2:19][C:20]3([OH:28])[CH2:21][CH2:22][S:23](=[O:27])(=[O:26])[CH2:24][CH2:25]3)=[CH:13][C:12]=2[CH3:29])=[CH:9][C:8]([CH2:30][NH:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][C:40]([OH:42])=[O:41])=[C:34]([F:45])[CH:33]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59434142HCID 59434142, compound

Product 1

HCID 59434134HCID 59434134, compoundYield 62.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of ethyl 3-{4-[({6-(acetylamino)-4′-[(4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy]-2′,6′-dimethylbiphenyl-3-yl}methyl)amino]-2-fluorophenyl}propanoate (173 mg, 0.27 mmol) in a mixture of methanol (1 mL) and tetrahydrofuran (2 mL) was added 1 M aqueous sodium hydroxide solution (0.81 mL), and the mixture was stirred overnight at room temperature. 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 (ethyl acetate-ethyl acetate/methanol=9/1) to give the title compound (103 mg, yield 62%) as a yellow 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 (ethyl acetate-ethyl acetate/methanol=9/1)

Sources & evidence

ORD record
ord-b1245fc636da428c99c22235563cb3d1
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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