Methanol → HCID 66898186, compound

HRID 1189033Notes

Reaction equation

HRID 1189033 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:28]=[N:29][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:31][CH:32]=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.O1CCCC1.CO.[BH4-].[Li+]>O>[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:28]=[N:29][C:30]([S:33]([CH3:36])(=[O:34])=[O:35])=[CH:31][CH:32]=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

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 66897908HCID 66897908, compound

Product 1

HCID 66898186HCID 66898186, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl {2-[7-(2-methoxy-1-methylethoxy)-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (660 mg), tetrahydrofuran (30 mL) and methanol (5 mL) was added lithium borohydride (130 mg) at 0° C. The whole was stirred at room temperature for 5 h. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:1 to 1:0, volume ratio) to give pale yellow crystals. The crystals were recrystallized from ethyl acetate-hexane to give the title compound (380 mg, 62%) as pale yellow prisms. MS 506 (MH+). mp 138-139° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=1:1 to 1:0, volume ratio)
  7. customto give pale yellow crystals
  8. customThe crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b69f8d02267a49e48b3cee8d33f1166b
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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