Water → HCID 58081023, compound

HRID 1042165Notes

Reaction equation

HRID 1042165 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][C:21]2[CH:22]=[N:23][C:24]([CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:25][CH:26]=2)=[CH:15][C:14]=3[O:32][CH:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[N:8][CH2:7]1)C.[BH4-].[Li+].O.C(OCC)(=O)C>O1CCCC1.CO.CCCCCC>[CH3:31][S:28]([CH2:27][C:24]1[N:23]=[CH:22][C:21]([O:20][C:16]2[CH:17]=[C:18]3[C:13](=[C:14]([O:32][CH:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH:15]=2)[NH:12][C:11]([C:9]2[S:10][CH:6]([CH2:5][CH2:4][OH:3])[CH2:7][N:8]=2)=[CH:19]3)=[CH:26][CH:25]=1)(=[O:29])=[O:30]

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 58081048HCID 58081048, compound

Product 1

HCID 58081023HCID 58081023, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of ethyl{2-[5-({6-[(methylsulfonyl)methyl]pyridin-3-yl}oxy)-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (290 mg) in tetrahydrofuran (10 mL) and methanol (15 mL) was added lithium tetrahydroborate (132 mg) at room temperature, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was subjected to basic silica gel column chromatography (ethyl acetate:hexane=0:100 to 100:0, volume ratio), and recrystallized from ethyl acetate to give the title compound (142 mg, yield 53%) as white crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crude product
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e820c165c0a348ca8f1555bb8f1b7388
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

Loading…