Methanol → HCID 53910850, compound

HRID 1646277Notes

Reaction equation

HRID 1646277 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[C:24]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:25]([O-:27])=[O:26])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.O1CCCC1.O.[OH-].[Li+]>O>[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[C:24]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:25]([OH:27])=[O:26])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86746477HCID 86746477, compound

Product 1

HCID 53910850HCID 53910850, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl, 7-(4,5-diphenyl-1H-imidazol-2-ylthio)-2-pentyl-2-heptenoate (0.37 g, 0.00078 mol) was combined with methanol (5 ml), tetrahydrofuran (2 ml) and lithium hydroxide monohydrate (0.16 g, 0.0038 mol) dissolved in water (3 ml), under a nitrogen atmosphere at ambient temperature. The reaction was heated to 50° for 4 hours, allowed to cool, concentrated then partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give an oil. The product was purified by flash chromatography eluting toluene: ethyl acetate: acetic acid (80:20:2) to give the title compound (0.22 g, 0.00049 mol, 63% yield) as a white foam. 1H NMR (CDCl3) δ7.5-7.4(d, 4H), 7.32-7.17(m, 7H), 6.77(t, 1H), 3.08(t, 2H), 2.3-2.15(m, 4H), 1.76-1.68(m, 2H), 1.57-1.50(m, 2H), 1.4-1.2(m, 6H), 0.87(t, 3H).

Workup

  1. temperatureThe reaction was heated to 50° for 4 hours
  2. temperatureto cool
  3. concentrationconcentrated
  4. customthen partitioned between ethyl acetate and saturated aqueous ammonium chloride
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give an oil
  9. customThe product was purified by flash chromatography
  10. washeluting toluene: ethyl acetate: acetic acid (80:20:2)

Sources & evidence

ORD record
ord-1e0435327d9e45f8b154bc7972c182ce
Source dataset
uspto-grants-1993_01
Patent number
US05179117

Reaction notes

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