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

HRID 1662055ノート

反応式

HRID 1662055 の反応式
[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]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydride2 回HCID 809722-Bromoethyl methyl ether2 回HCID 22643546Ethyl 3-[(tert-butoxycarbonyl)amino]benzoate

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-838617da2740488885246466c41f38ed
出典データセット
uspto-grants-2011_10
特許番号
US08030489B2

反応ノート

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