Potassium Carbonate → HCID 66990096, compound

HRID 454639Notes

Reaction equation

HRID 454639 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:15]([O:22][C:23]1[CH:50]=[CH:49][C:48]([CH2:51][CH2:52]Br)=[CH:47][C:24]=1[C:25]([NH:27][C:28]1[CH:40]=[C:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:38]=[CH:37][C:29]=1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(C)=O>[CH2:15]([O:22][C:23]1[CH:50]=[CH:49][C:48]([CH2:51][CH2:52][N:6]2[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]2)=[CH:47][C:24]=1[C:25]([NH:27][C:28]1[CH:40]=[C:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:38]=[CH:37][C:29]=1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 791961-Ethylpiperazine2×HCID 66990392HCID 66990392, compound

Product 1

HCID 66990096HCID 66990096, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Ethylpiperazine (0.065 mL) and potassium carbonate (0.042 g) were added to an acetone (1.2 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-(2-bromoethyl)benzamido)-4-phenylbenzoate (0.060 g), followed by stirring at room temperature for 6 hours. 1-Ethylpiperazine (0.065 mL) was added to the reaction mixture, followed by stirring at room temperature for 9 hours. The solvent was evaporated under reduced pressure, and a saturated aqueous solution of sodium bicarbonate and chloroform were added to the residue. The organic layer was separated and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol] to obtain 0.062 g of tert-butyl 2-(2-(benzyloxy)-5-(2-(4-ethylpiperazin-1-yl)ethyl)benzamido)-4-phenylbenzoate.

Workup

  1. stirringby stirring at room temperature for 9 hours
  2. customThe solvent was evaporated under reduced pressure
  3. additiona saturated aqueous solution of sodium bicarbonate and chloroform were added to the residue
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol]

Sources & evidence

ORD record
ord-b3cc348f2de6419fa8be38fa969f5601
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

Loading…