Tetrabutylammonium Fluoride → HCID 66975836, compound

HRID 1022690Notes

Reaction equation

HRID 1022690 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH2:20][C@H:21]1[C@H:27]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)[O:26][CH2:25][CH2:24][N:23]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:22]1)[C:12](=[O:19])[CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:35][C:30]1[CH:29]=[C:28]([C@@H:27]2[O:26][CH2:25][CH2:24][N:23]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:22][C@H:21]2[CH2:20][N:11]([CH2:10][CH2:9][OH:8])[C:12](=[O:19])[CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:33]=[CH:32][C:31]=1[Cl:34]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66976054HCID 66976054, compound

Product 1

HCID 66975836HCID 66975836, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (6R,7R)-6-{[(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)(pyrrolidin-1-ylacetyl)amino]methyl}-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (118 g) in THF (0.6 ml) was added, under ice-cooling, a solution (1.0 M, 0.219 ml) of tetrabutylammonium fluoride in THF, and the mixture was stirred at room temperature overnight. To the reaction mixture was added distilled water, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (NH, hexane/ethyl acetate/methanol) to give the title compound (81.3 mg).

Workup

  1. temperaturecooling
  2. additionTo the reaction mixture was added
  3. distillationdistilled water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with distilled water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (NH, hexane/ethyl acetate/methanol)

Sources & evidence

ORD record
ord-8be548777d2240c18279d92137fcfb43
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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