Tetrabutylammonium Fluoride → HCID 20094345, compound

HRID 273862Notes

Reaction equation

HRID 273862 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:34][CH2:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[O:43][CH2:44][CH3:45])[CH:9]([CH3:33])[CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([C:20]([NH2:22])=[O:21])[CH:19]=1)[N:16]([CH2:23][CH2:24][O:25][Si](C(C)(C)C)(C)C)[CH2:15][CH2:14]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([N:8]([CH2:34][CH2:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[O:43][CH2:44][CH3:45])[CH:9]([CH3:33])[CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([C:20]([NH2:22])=[O:21])[CH:19]=1)[N:16]([CH2:23][CH2:24][OH:25])[CH2:15][CH2:14]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 20094373HCID 20094373, compound

Product 1

HCID 20094345HCID 20094345, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]-1-[2-(tert-butyldimethylsiloxy)ethyl]indoline-7-carboxamide (170 mg) in tetrahydrofuran (2 ml) was added a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (270 μl), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using ethyl acetate as eluent to give 114 mg of 5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]-1-(2-hydroxyethyl)indoline-7-carboxamide as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by medium pressure liquid column chromatography on silica gel

Sources & evidence

ORD record
ord-5fc600557bf4438e9ddd2bb8875dcf37
Source dataset
uspto-grants-1995_02
Patent number
US05387603

Reaction notes

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