Methanol → HCID 67118649, compound

HRID 1189040Notes

Reaction equation

HRID 1189040 reaction equation
[F:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[C:9]2[C:5]([CH:6]=[C:7]([C:16]3[S:17][CH:18]([CH2:21][C:22]([O:24]CC)=[O:23])[CH2:19][N:20]=3)[NH:8]2)=[CH:4][C:3]=1[O:27][C:28]1[CH:29]=[N:30][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:32][CH:33]=1.O1CCCC1.CO.[OH-].[K+]>O>[F:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[C:9]2[C:5]([CH:6]=[C:7]([C:16]3[S:17][CH:18]([CH2:21][C:22]([OH:24])=[O:23])[CH2:19][N:20]=3)[NH:8]2)=[CH:4][C:3]=1[O:27][C:28]1[CH:29]=[N:30][C:31]([S:34]([CH3:37])(=[O:35])=[O:36])=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 70963860HCID 70963860, compound

Product 1

HCID 67118649HCID 67118649, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl {2-[6-fluoro-7-(2-methoxyethoxy)-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (0.30 g), tetrahydrofuran (12 mL) and methanol (12 mL) was added a solution of potassium hydroxide (85%, 0.18 g) in water (10 mL). The mixture was stirred at room temperature for 15 h and then partitioned between ethyl acetate and aqueous citric acid solution. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated to give a light yellow oil, which was crystallized from ethyl acetate-hexane to give the title compound (267 mg, 94%) as pale yellow crystals. MS 524 (MH+).

Workup

  1. custompartitioned between ethyl acetate and aqueous citric acid solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a light yellow oil, which
  7. customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-3a718910725c4109b4ba92e9f5ed0c2b
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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