Water → HCID 67119152, compound

HRID 1188990Notes

Reaction equation

HRID 1188990 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]1[S:15][CH:16]([CH2:19][C:20](OCC)=[O:21])[CH2:17][N:18]=1)=[CH:10]2)[CH3:3].[BH4-].[Li+].O>O1CCCC1.CO>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:25][C:26]2[CH:27]=[CH:28][C:29]([S:32]([CH3:35])(=[O:33])=[O:34])=[CH:30][CH:31]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]1[S:15][CH:16]([CH2:19][CH2:20][OH:21])[CH2:17][N:18]=1)=[CH:10]2)[CH3:1]

Participants

6

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 68381853HCID 68381853, compound

Product 1

HCID 67119152HCID 67119152, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (2-{7-(1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (330 mg) was dissolved in a mixture of tetrahydrofuran (15 mL) and methanol (3 mL). Lithium borohydride (30 mg) was added to the mixture at room temperature and the mixture was stirred at room temperature for 30 min. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90 to 80/20, volume ratio) to give the title compound (112 mg, 37%) as a pale yellow amorphous solid. MS 475 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90 to 80/20, volume ratio)

Sources & evidence

ORD record
ord-db629ab1a0e74b2ca082d47119e47cfd
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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