Water → HCID 57884476, compound

HRID 1818561Notes

Reaction equation

HRID 1818561 reaction equation
[OH-:1].[Li+].[C:3]([C:6]1[CH:29]=[CH:28][C:9]([O:10][CH2:11][C:12]2[CH:27]=[CH:26][C:15]([C:16]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([CH:25]=3)[C:23]#N)=[O:17])=[CH:14][CH:13]=2)=[C:8]([CH2:30][CH2:31][CH3:32])[C:7]=1[OH:33])(=[O:5])[CH3:4].[OH2:34]>O1CCOCC1.CCOCC>[C:3]([C:6]1[CH:29]=[CH:28][C:9]([O:10][CH2:11][C:12]2[CH:27]=[CH:26][C:15]([C:16]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([CH:25]=3)[C:23]([OH:34])=[O:1])=[O:17])=[CH:14][CH:13]=2)=[C:8]([CH2:30][CH2:31][CH3:32])[C:7]=1[OH:33])(=[O:5])[CH3:4]

Participants

6

Reactant 3

HCID 962Water2×HCID 3939Lithium HydroxideHCID 66699620HCID 66699620, compound

Product 1

HCID 57884476HCID 57884476, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Add lithium hydroxide (289 mg, 12.06 mmol) to a solution of 5-[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-benzoyl]-nicotinonitrile (500 mg, 1.21 mmol) in dioxane (10 mL) and water (10 mL) and stir. Heat solution to reflux. After 1 hour cool to ambient temperature, add water (100 mL) and wash with ethyl acetate. Acidify with 10% aqueous hydrochloric acid (15 mL), and extract with ethyl acetate. Combine organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to give a residue. Purify residue by sonicating in ether for 1 hour. Filter the resulting precipitate to yield the title compound as a beige solid (262 mg, 50%): 1H NMR (DMSO-d6) δ 0.86 (t, 3H), 1.48 (sextet, 2H), 2.54 (s, 3H), 2.59 (t, 2H), 5.38 (s, 2H), 6.70 (d, 1H), 7.62 (d, 2H), 7.79 (d, 1H), 7.84 (d, 2H), 8.42 (s, 1H), 9.05 (s, 1H), 9.24 (s, 1H), 12.82 (s, 1H), 13.72 (bs, 1H); MS (esi negative) m/z (rel intensity) 432 (100).

Workup

  1. temperatureHeat solution to reflux
  2. washwash with ethyl acetate
  3. extractionextract with ethyl acetate
  4. dry with materialCombine organic layers, dry with sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customto give a residue
  8. filtrationFilter the resulting precipitate

Sources & evidence

ORD record
ord-68f934ef12b04cb69e0cd96d4cf49e8e
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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