Acetone → Tert-butyl 2-(2-(methoxymethoxy)-5-methylbenzamido)-4-phenylbenzoate

HRID 454641Notes

Reaction equation

HRID 454641 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][CH2:9]Cl.CC(C)=O.[OH:15][C:16]1[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][C:17]=1[C:18]([NH:20][C:21]1[CH:33]=[C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:31]=[CH:30][C:22]=1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:19]>C(OCC)(=O)C.O>[CH3:7][O:8][CH2:9][O:15][C:16]1[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][C:17]=1[C:18]([NH:20][C:21]1[CH:33]=[C:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:31]=[CH:30][C:22]=1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:19]

Participants

7

Reactant 4

HCID 180AcetoneHCID 7864Chloromethyl Methyl Ether3×HCID 11430Potassium Carbonate3×HCID 58508560Tert-butyl 2-(2-hydroxy-5-methylbenzamido)-4-phenylbenzoate

Product 1

HCID 66991033Tert-butyl 2-(2-(methoxymethoxy)-5-methylbenzamido)-4-phenylbenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.51 g) and methoxymethyl chloride (0.23 mL) were sequentially added to an acetone (9.0 mL) suspension of tert-butyl 2-(2-hydroxy-5-methylbenzamido)-4-phenylbenzoate (0.60 g), followed by stirring at room temperature for 1 hour and 30 minutes. Potassium carbonate (0.21 g) and methoxymethyl chloride (0.11 mL) were sequentially added to the reaction mixture, followed by stirring at room temperature for 2 hours. Potassium carbonate (0.51 g) and methoxymethyl chloride (0.23 mL) were sequentially added to the reaction mixture, followed by stirring at room temperature for 2 hours and then heating to reflux for 20 minutes. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, 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: 100-80% hexane/ethyl acetate] to obtain 0.64 g of tert-butyl 2-(2-(methoxymethoxy)-5-methylbenzamido)-4-phenylbenzoate.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. stirringby stirring at room temperature for 2 hours
  3. temperatureheating
  4. temperatureto reflux for 20 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-80% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-491b5827e9324172984a4fd862c39e71
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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