Hydrochloric Acid → [[[[5-[(2,5-Difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridin-2-yl]carbonyl]amino]methoxy]acetic Acid

HRID 1641764Notes

Reaction equation

HRID 1641764 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:28]([C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)(=[O:30])=[O:29])[C:10]1[C:11]([CH3:27])=[CH:12][C:13]([C:16]([NH:18][CH2:19][O:20][CH2:21][C:22]([O:24]CC)=[O:23])=[O:17])=[N:14][CH:15]=1.O.[OH-].[Li+].Cl>O1CCCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:28]([C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)(=[O:30])=[O:29])[C:10]1[C:11]([CH3:27])=[CH:12][C:13]([C:16]([NH:18][CH2:19][O:20][CH2:21][C:22]([OH:24])=[O:23])=[O:17])=[N:14][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57736550Ethyl [[[[5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridin-2-yl]carbonyl]amino]methoxy]acetate

Product 1

HCID 57736415[[[[5-[(2,5-Difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridin-2-yl]carbonyl]amino]methoxy]acetic AcidYield 24.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of ethyl [[[[5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridin-2-yl]carbonyl]amino]methoxy]acetate (167 mg, 0.311 mmol) in tetrahydrofuran (6 ml) and water (3 ml), lithium hydroxide monohydrate (16 mg, 0.373 mmol) was added, and the mixture was stirred for 20 hours at room temperature. 1 N hydrochloric acid (0.5 ml) and water were added to the reaction solution, and the mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting concentration residue was subjected to flash silica gel column chromatography, and the fraction obtained from an elution with methanol:methylene chloride (=1:10) was concentrated under reduced pressure. A mixed solution of ethyl acetate-hexane was added to the resulting concentration residue, and then the residue was collected by filtration to obtain the title compound (38 mg, 0.075 mmol, 24%) as a white powder.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. concentrationThe resulting concentration residue
  6. customthe fraction obtained from an elution with methanol
  7. concentrationmethylene chloride (=1:10) was concentrated under reduced pressure
  8. additionA mixed solution of ethyl acetate-hexane was added to the resulting concentration residue
  9. filtrationthe residue was collected by filtration

Sources & evidence

ORD record
ord-bd1a446da869410990a710574b413b21
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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