Ammonium Chloride → HCID 23120650, compound

HRID 1662617Notes

Reaction equation

HRID 1662617 reaction equation
C(O[C:6](=[O:19])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=1)(C)(C)C.C([Li])(C)(C)C.[O:25]=[C:26]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][C:39]([F:42])([F:41])[F:40])C(OCC)=O.[NH4+].[Cl-]>CCOCC.CCCCC.C1COCC1>[Cl:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[C:15]([F:16])([F:17])[F:18])[NH:7][C:6](=[O:19])[C:26]2([OH:25])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][C:39]([F:40])([F:41])[F:42]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 10753918HCID 10753918, compoundHCID 21905863HCID 21905863, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 23120650HCID 23120650, compoundYield 64.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 4.00 g of tert-butyl[4-chloro-3-(trifluoromethyl)phenyl]carbamate in Et2O (30 ml) under cooling at −78° C. was added dropwise a solution of 1.6 mol/L tert-butyl lithium in n-pentane (21 ml), and the reaction mixture was stirred for 1 hour. Thereafter, the solution was warmed to −40° C. and was stirred under the same temperature condition for 2.5 hours. The solution was cooled again to −78° C., a solution of 4.25 g of ethyl oxo[2-(trifluoromethoxy)phenyl]acetate in THF (15 ml) was added dropwise to the reaction mixture and the reaction mixture was stirred under the same temperature condition for two hours. Thereafter, the solution was warmed to room temperature and stirred for 15 hours. To the reaction solution was added a saturated aqueous solution of NH4Cl, the resulting mixture was extracted with EtOAc, the organic layer was washed with saturated brine, dried over MgSO4 and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/4; v/v) to obtain 3.57 g of the title compound (colorless powder).

Workup

  1. stirringwas stirred under the same temperature condition for 2.5 hours
  2. temperatureThe solution was cooled again to −78° C.
  3. stirringthe reaction mixture was stirred under the same temperature condition for two hours
  4. temperatureThereafter, the solution was warmed to room temperature
  5. stirringstirred for 15 hours
  6. extractionthe resulting mixture was extracted with EtOAc
  7. washthe organic layer was washed with saturated brine
  8. dry with materialdried over MgSO4
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/4; v/v)

Sources & evidence

ORD record
ord-9ede728c9d2a4d949d566f282028b13c
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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