Acetone → Tert-butyl 4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-nitrobenzoate

HRID 454522노트

반응식

HRID 454522 반응식
[C:1](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.CC(C)=O.[C:18]([O:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]1[CH:44]=[CH:43][C:35]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[C:34]([N+:45]([O-:47])=[O:46])[CH:33]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>C(OCC)(=O)C.O>[C:18]([O:22][C:23]([N:25]([CH3:1])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]1[CH:44]=[CH:43][C:35]([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])=[C:34]([N+:45]([O-:47])=[O:46])[CH:33]=1)=[O:24])([CH3:19])([CH3:20])[CH3:21]

참가 물질

7

반응물 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 66990464Tert-butyl 4-(2-(tert-butoxycarbonylamino)phenyl)-2-nitrobenzoate

생성물 1

HCID 66990486Tert-butyl 4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-nitrobenzoate수율 21.9%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

Potassium carbonate (0.16 g) and dimethyl sulfate (0.094 mL) were added to an acetone (4.0 mL) solution of tert-butyl 4-(2-(tert-butoxycarbonylamino)phenyl)-2-nitrobenzoate (0.27 g), followed by heating to reflux for 2 hours. 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 [eluent: 95-85% hexane/ethyl acetate] and then purified by silica gel column chromatography [eluent: 91-85% hexane/ethyl acetate] to obtain 0.061 g of tert-butyl 4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-nitrobenzoate as a colorless oily substance.

후처리

  1. temperatureby heating
  2. temperatureto reflux for 2 hours
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate]
  8. custompurified by silica gel column chromatography [eluent: 91-85% hexane/ethyl acetate]

출처 및 근거

ORD 기록
ord-4c53a8d02bdd4556b2e057dd9a7c3710
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492582B2

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