Potassium bis(trimethylsilyl)amide → HCID 21963706, compound

HRID 2212213Notes

Reaction equation

HRID 2212213 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:19]([C:21]3[C:22]([C:27]4[C:32](F)=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:34])=[N:23][O:24][C:25]=3[CH3:26])=[O:20])[CH2:13]2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>CN(C)C=O>[Cl:34][C:28]1[C:27]2[C:22]3[C:21](=[C:25]([CH3:26])[O:24][N:23]=3)[C:19](=[O:20])[N:18]([CH:14]3[CH2:15][CH2:16][CH2:17][N:12]([C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:13]3)[C:32]=2[CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 21963707HCID 21963707, compound

Product 1

HCID 21963706HCID 21963706, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 3-(2-chloro-6-fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid[1-(4-phenyl-butyryl)-piperidin-3-yl]-amide (300 mg, 0.62 mmol) in N,N-dimethyl-formamide (4 mL) at ambient temperature under a nitrogen atmosphere. Add a solution of potassium bis(trimethylsilyl)amide (0.5 M in toluene, 1.49 mL, 0.75 mmol) and stir for 20 min. at ambient temperature. Quench with water and follow by adding of solid sodium chloride. Extract with ethyl acetate and wash with water and dry over sodium sulfate. Concentrate and elute over silica gel to give 83 mg (29%) of the desired product. MS(ES): (M+1)+ 464.1, 466.1 m/z.

Workup

  1. customQuench with water
  2. additionby adding of solid sodium chloride
  3. extractionExtract with ethyl acetate
  4. washwash with water
  5. dry with materialdry over sodium sulfate
  6. concentrationConcentrate
  7. washelute over silica gel

Sources & evidence

ORD record
ord-d1e9d9eb0f334cb5951cdb5f53084938
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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