Methanol → HCID 68381622, compound

HRID 1188981Notes

Reaction equation

HRID 1188981 reaction equation
C([Si](C(C)(C)C)(C1C=CC=CC=1)[O:6][CH2:7][CH:8]([CH3:38])[O:9][C:10]1[CH:11]=[C:12]([O:27][C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][CH:29]=2)[CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]([CH2:24][CH2:25][OH:26])[CH2:22][N:23]=1)=[CH:15]2)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+].CO>O1CCCC1.CCCCCC.C(OCC)(=O)C>[OH:26][CH2:25][CH2:24][CH:21]1[S:20][C:19]([C:16]2[NH:17][C:18]3[C:14]([CH:15]=2)=[CH:13][C:12]([O:27][C:28]2[CH:29]=[CH:30][C:31]([S:34]([CH3:37])(=[O:35])=[O:36])=[CH:32][CH:33]=2)=[CH:11][C:10]=3[O:9][CH:8]([CH3:38])[CH2:7][OH:6])=[N:23][CH2:22]1

Participants

8

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 67118535HCID 67118535, compound

Product 1

HCID 68381622HCID 68381622, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 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)ethanol (270 mg) was dissolved in tetrahydrofuran (2 mL), tetrabutylammonium fluoride (0.6 mL) was added, and the mixture was stirred at room temperature for 18 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:hexane=0:20:80 to 5:95:0, volume ratio) to give the title compound (117 mg, yield 65%) as a white solid. The obtained white solid was recrystallized from ethyl acetate-diethyl ether to give colorless crystals. melting point 165-169° C. MS 491 (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-7ca6fea3468142908e0956a83e7b49f4
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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