Potassium Carbonate → Methyl 2-(2-(benzyloxy)-5-(2-(thiomorpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate

HRID 454700Notes

Reaction equation

HRID 454700 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:12][CH2:11][S:10][CH2:9][CH2:8]1.[CH2:13]([O:20][C:21]1[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48]Br)=[CH:42][C:22]=1[C:23]([NH:25][C:26]1[CH:35]=[C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:33]=[CH:32][C:27]=1[C:28]([O:30][CH3:31])=[O:29])=[O:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC(C)=O>[CH2:13]([O:20][C:21]1[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][N:7]2[CH2:12][CH2:11][S:10][CH2:9][CH2:8]2)=[CH:42][C:22]=1[C:23]([NH:25][C:26]1[CH:35]=[C:34]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:33]=[CH:32][C:27]=1[C:28]([O:30][CH3:31])=[O:29])=[O:24])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67164Thiomorpholine2×HCID 66990627Methyl 2-(2-(benzyloxy)-5-(2-bromoethoxy)benzamido)-4-phenylbenzoate

Product 1

HCID 66990890Methyl 2-(2-(benzyloxy)-5-(2-(thiomorpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (2.0 g) and thiomorpholine (1.1 mL) were added to an acetone (20 mL) solution of methyl 2-(2-(benzyloxy)-5-(2-bromoethoxy)benzamido)-4-phenylbenzoate (2.0 g), followed by heating to reflux for 4 hours. The reaction mixture was cooled to room temperature, and thiomorpholine (0.55 mL) was added thereto, followed by heating to reflux for 2 hours and 30 minutes. After cooling the reaction mixture to room temperature, the solvent was evaporated under reduced pressure, and water and chloroform were added to the residue. The organic layer was separated and dried over anhydrous magnesium 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: 70-40% hexane/ethyl acetate] to obtain 1.9 g of methyl 2-(2-(benzyloxy)-5-(2-(thiomorpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate as a white solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 4 hours
  3. temperatureby heating
  4. temperatureto reflux for 2 hours and 30 minutes
  5. temperatureAfter cooling the reaction mixture to room temperature
  6. customthe solvent was evaporated under reduced pressure, and water and chloroform
  7. additionwere added to the residue
  8. customThe organic layer was separated
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 70-40% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-f88174115a564b7eb9d75e6ffa9f7dab
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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