Ethyl bromoacetate → Diethyl 2-(((benzyloxy)carbonyl)amino)-2-cyanosuccinate

HRID 256599Notes

Reaction equation

HRID 256599 reaction equation
[O-]CC.[Na+].[Na].[CH2:6]([O:8][C:9](=[O:24])[CH:10]([NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C:11]#[N:12])[CH3:7].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(O)C>[CH2:6]([O:8][C:9](=[O:24])[C:10]([NH:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])([C:11]#[N:12])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:7]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 9943163Ethyl 2-(((benzyloxy)carbonyl)amino)-2-cyanoacetate

Product 1

HCID 10712704Diethyl 2-(((benzyloxy)carbonyl)amino)-2-cyanosuccinateYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To a sodium ethoxide solution, which was prepared from sodium (2.11 g) and ethanol (400 ml), were added in turn 2-benzyloxycarbonylamino-2-cyanoacetic acid ethyl ester (24.0 g) and ethyl bromoacetate (15.3 g). The resulting mixture was stirred at 25° C. for 3 hours and concentrated under reduced pressure. The residue was diluted with water and extracted with chloroform. The extracts were washed with water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to give the title compound (31.6 g, 99%) as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with chloroform
  4. washThe extracts were washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8e8d8fca338c492d9237471db9e0f0b4
Source dataset
uspto-grants-1993_11
Patent number
US05258382

Reaction notes

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