Water → HCID 87212338, compound

HRID 536652Notes

Reaction equation

HRID 536652 reaction equation
CI.[F:3][C:4]([F:28])([F:27])[C:5]([N:7]1[CH2:14][CH2:13][C@:12]2([CH3:18])[C:15]([CH3:17])([CH3:16])[C@H:8]1[CH2:9][C:10]1[C:22]([OH:23])=[C:21]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:19][C:11]=12)=[O:6].[C:29](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[F:28][C:4]([F:3])([F:27])[C:5]([N:7]1[CH2:14][CH2:13][C@:12]2([CH3:18])[C:15]([CH3:17])([CH3:16])[C@H:8]1[CH2:9][C:10]1[C:22]([O:23][CH3:29])=[C:21]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:19][C:11]=12)=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 58123826HCID 58123826, compound

Product 1

HCID 87212338HCID 87212338, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl iodide (80 μL) is added to a mixture of (2R,6S)-2,2,2-trifluoro-1-(10-hydroxy-6,11,11-trimethyl-9-nitro-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl)-ethanone (0.40 g) and potassium carbonate (0.17 g) in dimethylformamide (5 mL). The mixture is stirred at room temperature overnight, before another portion of methyl iodide (80 μL) and potassium carbonate (0.16 g) are added. The mixture is stirred for another 6 h at room temperature. Then, water and ethyl acetate are added, the organic phase is separated, and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with brine and dried (Na2SO4). The solvent is evaporated to give the crude product that is used without further purification.

Workup

  1. additionare added
  2. customthe organic phase is separated
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent is evaporated

Sources & evidence

ORD record
ord-512b15e37a124f43b0d5c724367d5352
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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