Sodium hydride → HCID 69932760, compound

HRID 2227396Notes

Reaction equation

HRID 2227396 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][NH:13][C:12](=[O:16])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[C:17]([Si:21]([O:34][C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([CH2:42]Br)[CH:36]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:20])([CH3:19])[CH3:18]>CCCCCC.CN(C=O)C>[Si:21]([O:34][C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([CH:36]=1)[CH2:42][N:13]1[CH2:14][CH2:15][N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])[CH2:11][C:12]1=[O:16])([C:17]([CH3:19])([CH3:20])[CH3:18])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 11155397HCID 11155397, compound

Product 1

HCID 69932760HCID 69932760, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil) (3.50 g, 0.0874 mmol) was washed with hexane, suspended in DMF (100 mL) at 0° C. with stirring under Ar, then treated with tert-Butyl-3-oxopiperazine-1-carboxylate (15.0 g, 0.728 mol). After 1 h, tert-butyl(3-bromomethyl-4-chlorophenoxy) diphenylsilane (33.34 g, 0.0728 mol) in DMF (50 mL) was added dropwise, and the reaction mixture was left to warm to room temperature overnight. The reaction mixture partitioned between EtOAc/hexane (50/50) and H2O, the aqueous layer washed with EtOAc/hexane, the organics combined, washed with H2O, brine, and dried (Na2SO4). Filtration and concentration to dryness gave the title compound which was used without purification.

Workup

  1. waitthe reaction mixture was left
  2. customThe reaction mixture partitioned between EtOAc/hexane (50/50) and H2O
  3. washthe aqueous layer washed with EtOAc/hexane
  4. washwashed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-c01c547a27294b4197740527d1da4c05
Source dataset
uspto-grants-2002_07
Patent number
US06413964B1

Reaction notes

Loading…