Methanol → HCID 58237013, compound

HRID 1189049Notes

Reaction equation

HRID 1189049 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][C:18]([O:20]CC)=[O:19])[CH2:15][N:16]=1)=[CH:8]2.O1CCCC1.CO.[OH-].[K+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][C:18]([OH:20])=[O:19])[CH2:15][N:16]=1)=[CH:8]2

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 58236985HCID 58236985, compound

Product 1

HCID 58237013HCID 58237013, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl (2-{7-methoxy-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (0.42 g), tetrahydrofuran (8 mL) and methanol (8 mL) was added a solution of potassium hydroxide (85%, 0.25 g) in water (5 mL). The mixture was stirred at room temperature for 15 h and concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated to give a light amorphous solid, which was crystallized from ethyl acetate-hexane to give the title compound (340 mg, 86%) as pale yellow crystals. MS 461 (MH+). mp 144-145° C.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a light amorphous solid, which
  8. customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1ea5b69240f34bfeae9455cd65b7d589
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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