Methanol → HCID 86652856, compound

HRID 1188982Notes

Reaction equation

HRID 1188982 reaction equation
C([Si](C(C)(C)C)(C1C=CC=CC=1)[O:6][CH2:7][CH:8]([CH3:39])[O:9][C:10]1[CH:11]=[C:12]([O:28][C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=2)[CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]([CH2:24][C:25]([NH2:27])=[O:26])[CH2:22][N:23]=1)=[CH:15]2)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+].CO>O1CCCC1.C(OCC)(=O)C>[OH:6][CH2:7][CH:8]([CH3:39])[O:9][C:10]1[CH:11]=[C:12]([O:28][C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:36])=[O:37])=[CH:31][CH:30]=2)[CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]([CH2:24][C:25]([NH2:27])=[O:26])[CH2:22][N:23]=1)=[CH:15]2

Participants

7

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 67118826HCID 67118826, compound

Product 1

HCID 86652856HCID 86652856, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(2-{7-(2-{[Di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl)acetamide (262 mg) was dissolved in tetrahydrofuran (2 mL), tetrabutylammonium fluoride (0.5 mL) was added, and the mixture was stirred at room temperature for 15 hr. Saturated aqueous ammonium chloride solution was added to the reaction solution, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtrated, and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (methanol:ethyl acetate=0:100 to 10:90, volume ratio) to give the title compound (144 mg, yield 81%) as a white solid. The obtained white solid was recrystallized from ethyl acetate-hexane to give colorless crystals. melting point 137-142° C. MS 504 (MH+).

Workup

  1. extractionthe mixture was subjected to extraction 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. filtrationfiltrated
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crude product

Sources & evidence

ORD record
ord-b0c5060480974e66b35cddd993449e67
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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