Potassium Carbonate → Ethyl 2-{[di(tert-butoxycarbonyl)amino]methyl}acrylate

HRID 80598

Reaction equation

HRID 80598 reaction equation
Br[CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:21]([O:20][C:18]([N:10]([CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 279800Di-tert-butyl IminodicarboxylateHCID 3106202-(Bromomethyl)acrylic acid ethyl ester

Product 1

HCID 86672207Ethyl 2-{[di(tert-butoxycarbonyl)amino]methyl}acrylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To ethyl 2-(bromomethyl)acrylate (104.4 g) in an acetonitrile (900 ml) solution, di-tert-butyl imino dicarboxylate (122.4 g) and potassium carbonate was added, and the mixture was stirred at room temperature for 2 days. The reaction solution was concentrated in vacuo. To the residue, ethyl acetate (1.4 liter) and water (700 ml) were added, and the layers were separated. The organic layer was washed with water (350 ml), dried over sodium sulfate, then concentrated to obtain ethyl 2-{[di(tert-butoxycarbonyl)amino]methyl}acrylate (compound S62a) as a crude product (182.7 g).

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additionTo the residue, ethyl acetate (1.4 liter) and water (700 ml) were added
  3. customthe layers were separated
  4. washThe organic layer was washed with water (350 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ffde7a9591174629b70fbf52587ce0f1
Source dataset
uspto-grants-2014_09
Patent number
US08846660B2

Linked notes

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