Dimethylformamide → Ethyl 3-[(tert-butoxycarbonyl)(2-methoxyethyl)amino]benzoate

HRID 1662055노트

반응식

HRID 1662055 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C=O)C.[H-].[Na+].Br[CH2:28][CH2:29][O:30][CH3:31]>C(OCC)(=O)C.O>[C:1]([O:5][C:6]([N:8]([CH2:28][CH2:29][O:30][CH3:31])[C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydride2회HCID 809722-Bromoethyl methyl ether2회HCID 22643546Ethyl 3-[(tert-butoxycarbonyl)amino]benzoate

생성물 1

HCID 59453987Ethyl 3-[(tert-butoxycarbonyl)(2-methoxyethyl)amino]benzoate수율 58.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of ethyl 3-[(tert-butoxycarbonyl)amino]benzoate (3.8 g) and DMF (20 ml) were added 60% sodium hydride (1.1 g) and 2-bromoethylmethyl ether (3.9 g) under ice-cooling, followed by stirring at room temperature over one night. To the reaction mixture were added 60% sodium hydride (0.28 g) and 2-bromoethylmethyl ether (0.98 g), followed by stirring at room temperature for 6 hours. Water and ethyl acetate were added thereto, and the organic layer was then separated, washed with 1 M hydrochloric acid and saturated brine in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain ethyl 3-[(tert-butoxycarbonyl)(2-methoxyethyl)amino]benzoate (2.7 g).

후처리

  1. temperaturecooling
  2. stirringby stirring at room temperature for 6 hours
  3. customthe organic layer was then separated
  4. washwashed with 1 M hydrochloric acid and saturated brine in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-838617da2740488885246466c41f38ed
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030489B2

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