Potassium Hydroxide → 3-[2,6-Difluoro-4-[[4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzyl]oxy]phenyl]propanoic acid

HRID 732222Notes

Reaction equation

HRID 732222 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:18]3[S:19][CH:20]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:22]=3)=[CH:12][CH:11]=2)[CH:5]=[C:4]([F:37])[C:3]=1[CH2:38][CH2:39][C:40]([O:42]CC)=[O:41].[OH-].[K+]>O1CCCC1.C(O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:18]3[S:19][CH:20]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:22]=3)=[CH:12][CH:11]=2)[CH:5]=[C:4]([F:37])[C:3]=1[CH2:38][CH2:39][C:40]([OH:42])=[O:41]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 23143263Ethyl 3-[2,6-difluoro-4-[[4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzyl]oxy]phenyl]-propanoate

Product 1

HCID 114446463-[2,6-Difluoro-4-[[4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzyl]oxy]phenyl]propanoic acidYield 94.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

That is, ethyl 3-[2,6-difluoro-4-[[4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzyl]oxy]phenyl]-propanoate (300 mg, 0.49 mmol) was dissolved in a mixed solvent of tetrahydrofuran (8 mL) and ethanol (8 mL). Thereto was added an aqueous solution (5 mL) of 85% potassium hydroxide (100 mg, 1.51 mmol), and the mixture was stirred at room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, washed successively with aqueous citric acid solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and crystallized from diethyl ether-hexane to give the title compound (271 mg, yield 94%) as colorless prism crystals.

Workup

  1. washwashed successively with aqueous citric acid solution, water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. customcrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-d144101098c144e38a515910f84201e2
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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