Water → HCID 44236794, compound

HRID 1189015Notes

Reaction equation

HRID 1189015 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](OCC)=[O:22])[CH2:18][N:19]=1)=[CH:11]2.[BH4-].[Li+].O>O1CCCC1>[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][CH2:21][OH:22])[CH2:18][N:19]=1)=[CH:11]2

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydride2×HCID 58236999HCID 58236999, compound

Product 1

HCID 44236794HCID 44236794, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution 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 (277 mg) in tetrahydrofuran (5 mL) was added lithium borohydride (55 mg) at 0° C. After stirring at 0° C. for 1.5 h, lithium borohydride (22 mg) was added to the mixture. The whole was stirred at 0° C. for 2 h, at room temperature for 2.5 h, and then at 50° C. overnight. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:methanol=100:0 to 95:5, volume ratio) to give the title compound (37% mg, 15%) as a white amorphous solid. MS 505 (MH+).

Workup

  1. stirringThe whole was stirred at 0° C. for 2 h, at room temperature for 2.5 h
  2. customat 50° C.
  3. customovernight
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography (ethyl acetate:methanol=100:0 to 95:5, volume ratio)

Sources & evidence

ORD record
ord-25f3d55e627b4626b9bf8a49c738fd9a
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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