Fluoride Ion → HCID 18753489, compound

HRID 1838429Notes

Reaction equation

HRID 1838429 reaction equation
[F-].[Si]([O:9][CH2:10][CH:11]([N:24]([CH3:41])[S:25]([C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23])(C(C)(C)C)(C)C>O1CCCC1>[OH:9][CH2:10][CH:11]([N:24]([CH3:41])[S:25]([C:28]1[CH:29]=[CH:30][C:31]([O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:32][CH:33]=1)(=[O:26])=[O:27])[CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23]

Participants

4

Reactant 2

HCID 28179Fluoride IonHCID 18753594HCID 18753594, compound2×

Product 1

HCID 18753489HCID 18753489, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

After addition of 1M solution of tetrabutylanimonium fluoride (19.11 ml, 19.11 mmol) in tetrahydrofuran to a solution of (±)-1-(tert-butyldimethylsilyloxymethyl)-N-methyl-N-(4-phenoxybenzenesulfonyl)-2-phthalimidoethylamine (7.40 g, 12.74 mmol), the product of (4) above, in tetrahydrofuran (50 ml), the mixture was stirred at room temperature for 1 hour. The solvent of the reaction mixture was evaporated under reduced pressure. To the resulting residue, water was added and this was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=2/1 as the eluant to afford the desired compound (1.70 g, yield 29%) as a white powder.

Workup

  1. customThe solvent of the reaction mixture was evaporated under reduced pressure
  2. additionTo the resulting residue, water was added
  3. extractionthis was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-707f619cb6214185947076a56c4c2eeb
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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