Hydrochloric Acid → HCID 57884475, compound

HRID 1818564Notes

Reaction equation

HRID 1818564 reaction equation
[OH-:1].[Li+].[C:3]([C:6]1[CH:29]=[CH:28][C:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([OH:27])C3C=NC=C(C=3)C#N)=[CH:14][CH:13]=2)=[C:8]([CH2:30][CH2:31][CH3:32])[C:7]=1[OH:33])(=[O:5])[CH3:4].[OH2:34].Cl.[C:36](#[N:38])[CH3:37]>O1CCOCC1.C(OCC)(=O)C>[C:3]([C:6]1[CH:29]=[CH:28][C:9]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]([OH:27])[C:37]3[CH:36]=[N:38][CH:3]=[C:6]([CH:7]=3)[C:29]([OH:34])=[O:1])=[CH:16][CH:17]=2)=[C:8]([CH2:30][CH2:31][CH3:32])[C:7]=1[OH:33])(=[O:5])[CH3:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 6342AcetonitrileHCID 66699577HCID 66699577, compound

Product 1

HCID 57884475HCID 57884475, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Add lithium hydroxide (1M aqueous solution, 11.4 mL, 11.4 mmol) to a solution of 5-{[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-nicotinonitrile (473 mg, 1.14 mmol) in dioxane (10 mL). Heat reaction to 80° C. After 2 hours, cool to room temperature and pour into water (50 ml). Wash solution with ethyl acetate (25 mL), and discard. Acidify the aqueous layer with 10% hydrochloric acid, and extract with 25% isopropyl alcohol:75% dichloromethane. Combine the organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to give a residue. Sonicate the residue in acetonitrile (10 mL), and filter to yield the title compound as a beige solid (210 mg, 42%): 1H NMR (DMSO-d6) δ 0.86 (t, 3H), 1.47 (sextet, 2H), 2.55-2.59 (m, 5H), 5.22 (bs, 2H), 5.90 (bs, 1H), 6.70 (d, 1H), 7.43 (q, 4H), 7.79 (d, 1H), 8.21 (t, 1H), 8.82 (d, 1H), 8.92 (d, 1H), 12.84 (s, 1H); MS (esi negative) m/z (rel intensity) 434 (100).

Workup

  1. temperatureHeat
  2. customreaction to 80° C
  3. extractionextract with 25% isopropyl alcohol
  4. dry with materialdry with sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customto give a residue
  8. filtrationfilter

Sources & evidence

ORD record
ord-6e8dc097a5be48d4b38a9b631e59d0df
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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