Water → HCID 17861989, compound

HRID 2109345Notes

Reaction equation

HRID 2109345 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][CH2:8][CH:9]1[C:15]2[CH:16]=[CH:17][C:18]([O:20][C:21](=[O:25])[N:22]([CH3:24])[CH3:23])=[CH:19][C:14]=2[CH:13]=[CH:12][CH2:11][N:10]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH3:24][N:22]([CH3:23])[C:21]([O:20][C:18]1[CH:17]=[CH:16][C:15]2[CH:9]([CH2:8][CH2:7][OH:6])[N:10]([C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])[CH2:11][CH:12]=[CH:13][C:14]=2[CH:19]=1)=[O:25]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 57519124HCID 57519124, compound

Product 1

HCID 17861989HCID 17861989, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of t-butyl 1-[2-(t-butyl-diphenyl-silanyloxy)-ethyl]-7-dimethylcarbamoyloxy-1,3-dihydro-benzo[c]azepine-2-carboxylate (1.82 g, 2.96 mmol) synthesized in step (k) of Example 192 in tetrahydrofuran (10 ml) was added 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (6.0 ml, 6.0 mmol) at room temperature, and the resulting mixture was stirred for 1 hour at room temperature under a nitrogen atmosphere. After stirring, water (30 ml) was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate (40 ml×2). The organic layer was washed successively with water (40 ml×1) and saturated aqueous sodium chloride solution (40 ml×1), dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to afford the crude product. The crude product was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (1:1-0:1) as the eluent to afford the title compound (1.07 g, yield: 96%) as a colorless oil.

Workup

  1. stirringAfter stirring
  2. extractionthe resulting mixture was extracted with ethyl acetate (40 ml×2)
  3. washThe organic layer was washed successively with water (40 ml×1) and saturated aqueous sodium chloride solution (40 ml×1)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford the crude product
  8. customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-cbcf4d1aa3534f469cc0b00262e97f83
Source dataset
uspto-grants-2009_04
Patent number
US07514475B2

Reaction notes

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