Potassium trimethylsilanolate → HCID 57555239, compound

HRID 220855Notes

Reaction equation

HRID 220855 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:28])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25]C)=[O:24])=[C:19]([Cl:27])[CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)[O-].[K+].[SiH3][O-].[K+]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:28])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[C:19]([Cl:27])[CH:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 23668039Potassium trimethylsilanolateHCID 575553524-[2-(3-Chloro-4-methoxycarbonyl-phenoxy)-acetyl]-piperazine-1-carboxylic Acid Tert-butyl EsterHCID 131729785HCID 131729785, compound2×

Product 1

HCID 57555239HCID 57555239, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-[2-(3-Chloro-4-methoxycarbonyl-phenoxy)-acetyl]-piperazine-1-carboxylic acid tert-butyl ester from Example E41c.1 (4.5 g, 10.8 mmol) in THF at 0° C. was treated with potassium trimethylsilanolate (1.6 g, 10.9 mmol), and the mixture stirred at room temperature for 18 h. A further 1.6 g (10.9 mmol) potassium silanolate was added, and stirring continued at room temperature for 2 h. A further 1.6 g (10.9 mmol) potassium silanolate was added, and the mixture was stirred at 45° C. for 2 h. The mixture was then diluted with water and THF was removed in vacuo. The residue was washed with ether, cooled in an ice-bath and adjusted to pH5 with solid KHSO4 whereupon it was extracted with CHCl3 and CHCl3/isopropanol (90:10 v/v). The combined organics were dried and solvents were removed in vacuo to yield the title compound (3.7 g, 85%).

Workup

  1. customat 0° C.
  2. stirringstirring
  3. waitcontinued at room temperature for 2 h
  4. stirringthe mixture was stirred at 45° C. for 2 h
  5. customwas removed in vacuo
  6. washThe residue was washed with ether
  7. temperaturecooled in an ice-bath
  8. extractionwas extracted with CHCl3 and CHCl3/isopropanol (90:10 v/v)
  9. customThe combined organics were dried
  10. customsolvents were removed in vacuo

Sources & evidence

ORD record
ord-35483664abd24b0ba96a72ee7a4222fc
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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