Ammonium Chloride → HCID 68503951, compound

HRID 1715419Notes

Reaction equation

HRID 1715419 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([SiH2][O:24][C:25](C)(C)[C:26]1[CH:27]=[C:28]([CH2:33][CH2:34][NH:35][C:36](=[O:42])[CH2:37][C:38]([F:41])([F:40])[F:39])[CH:29]=[CH:30][C:31]=1[Cl:32])(C)(C)C.[NH4+].[Cl-]>C1COCC1>[Cl:32][C:31]1[CH:30]=[CH:29][C:28]([CH2:33][CH2:34][NH:35][C:36](=[O:42])[CH2:37][C:38]([F:41])([F:40])[F:39])=[CH:27][C:26]=1[CH2:25][OH:24]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 137329924HCID 137329924, compound

Product 1

HCID 68503951HCID 68503951, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

TBAF (1M in THF, 2.46 mL, 2.46 mmol) was added to a sol. of N-{2-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-phenyl]-ethyl}-3,3,3-trifluoro-propionamide (500 mg, 1.22 mmol) in THF (15.8 mL) at 0° C. The mixture was stirred for 1 h at 0° C., and aq. sat. NH4Cl was added. The mixture was extracted with EtOAc (3×). The combined org. extracts were washed with water (4×), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (CH2Cl2/MeOH 19:1) yielded the title compound (230 mg, 64%). LC-MS: tR=0.79 min.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×)
  2. washextracts were washed with water (4×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (CH2Cl2/MeOH 19:1)

Sources & evidence

ORD record
ord-a06bdb40268746aca066dba84c464391
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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