Potassium Carbonate → HCID 66990525, compound

HRID 454686Notes

Reaction equation

HRID 454686 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][OH:11].[CH2:12]([O:19][C:20]1[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH2:47][N:48]2[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]2)=[CH:41][C:21]=1[C:22]([NH:24][C:25]1[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28])=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CC(=O)CC>[CH2:12]([O:19][C:20]1[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH2:47][N:48]2[CH2:53][CH2:52][N:51]([CH2:8][CH2:9][CH2:10][OH:11])[CH2:50][CH2:49]2)=[CH:41][C:21]=1[C:22]([NH:24][C:25]1[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28])=[O:23])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 516892Sodium BicarbonateHCID 66990307HCID 66990307, compound

Product 1

HCID 66990525HCID 66990525, compound

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.031 g) and 3-bromo-1-propanol (0.013 mL) were added to a 2-butanone (1.3 mL) solution of methyl 2-(2-(benzyloxy)-5-(2-(piperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate (0.084 g), followed by heating to reflux for 1 hour. The reaction mixture was cooled to room temperature, and then a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-91% chloroform/methanol] to obtain 0.036 g of methyl 2-(2-(benzyloxy)-5-(2-(4-(3-hydroxypropyl)piperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate as a light yellow oily substance.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 1 hour
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  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 [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-91% chloroform/methanol]

Sources & evidence

ORD record
ord-93a208eab0ce41ce9f0c46d6c432aab7
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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