Tetrahydrofuran → HCID 58237049, compound

HRID 1189013Notes

Reaction equation

HRID 1189013 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([CH3:37])[O:5][C:6]1[CH:7]=[C:8]([O:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]1[S:16][CH:17]([CH2:20][C:21]([O:23]CC)=[O:22])[CH2:18][N:19]=1)=[CH:11]2.O1CCCC1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][CH2:3][CH:4]([CH3:37])[O:5][C:6]1[CH:7]=[C:8]([O:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]1[S:16][CH:17]([CH2:20][C:21]([OH:23])=[O:22])[CH2:18][N:19]=1)=[CH:11]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58236999HCID 58236999, compound

Product 1

HCID 58237049HCID 58237049, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl (2-{7-(2-methoxy-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (134 mg), tetrahydrofuran (1 mL) and ethanol (1 mL) was added 1M aqueous sodium hydroxide solution (0.51 mL). The whole was stirred at room temperature for 2 h, and then concentrated in vacuo. The residue was acidified by 1M hydrochloric acid, and then extracted with ethyl acetate-tetrahydrofuran. The organic layer was washed successively with water and brine, dried (MgSO4), filtered, and concentrated in vacuo to give the title compound (57 mg, 43%) as a yellow amorphous solid. MS 519 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate-tetrahydrofuran
  3. washThe organic layer was washed successively with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-acdaf37f68b2488e910bd87379e732eb
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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