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

HRID 1662055Notes

Reaction equation

HRID 1662055 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-838617da2740488885246466c41f38ed
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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