Tetrabutylammonium Fluoride → HCID 69202719, compound

HRID 2220655Notes

Reaction equation

HRID 2220655 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Br:19][C:20]1[CH:68]=[CH:67][C:23]([O:24][CH2:25][C:26]([NH:28][CH2:29][C@@H:30]([C:39]2[CH:44]=[CH:43][C:42]([O:45][CH2:46][O:47][CH2:48][CH2:49][Si:50]([CH3:53])([CH3:52])[CH3:51])=[C:41]([N:54]([S:63]([CH3:66])(=[O:65])=[O:64])[CH2:55][O:56][CH2:57][CH2:58][Si:59]([CH3:62])([CH3:61])[CH3:60])[CH:40]=2)[O:31][Si](CC)(CC)CC)=[O:27])=[CH:22][CH:21]=1>O1CCCC1>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH2:25][C:26]([NH:28][CH2:29][C@H:30]([OH:31])[C:39]2[CH:44]=[CH:43][C:42]([O:45][CH2:46][O:47][CH2:48][CH2:49][Si:50]([CH3:53])([CH3:52])[CH3:51])=[C:41]([N:54]([S:63]([CH3:66])(=[O:65])=[O:64])[CH2:55][O:56][CH2:57][CH2:58][Si:59]([CH3:60])([CH3:61])[CH3:62])[CH:40]=2)=[O:27])=[CH:67][CH:68]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 69200757HCID 69200757, compound

Product 1

HCID 69202719HCID 69202719, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1 mol/L solution of tetra-n-butylammonium fluoride (2.6 mL) was added to a solution of 2-(4-bromophenoxy)-N—((R)-2-{3-[methanesulfonyl(2-trimethylsilylethoxymethyl)amino]-4-(2-trimethylsilylethoxymethoxy)phenyl}-2-triethylsilyloxyethyl)acetamide (2.37 g) in tetrahydrofuran (8 mL), and the mixture was stirred at room temperature for 2.5 hrs. A 1 mol/L solution of tetra-n-butylammonium fluoride (0.67 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 12 hrs. The reaction mixture was concentrated in vacuo, and water was added to the residue. The mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium-pressure silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to afford the title compound (1.71 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hrs
  2. concentrationThe reaction mixture was concentrated in vacuo, and water
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by medium-pressure silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-48358b6301634f828107c484282cfe76
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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