Acetic-formic anhydride → Ethyl N-formyl-3-nitriloalaninate

HRID 1674707Notes

Reaction equation

HRID 1674707 reaction equation
[N:1]#[C:2][C@@H:3]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH2:4].[CH:10](OC(=O)C)=[O:11]>CCOCC>[CH:10]([NH:4][C@H:3]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:2]#[N:1])=[O:11]

Participants

4

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 931182Ethyl 3-nitriloalaninate

Product 1

HCID 86619658Ethyl N-formyl-3-nitriloalaninate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl 3-nitriloalaninate (26.9 g, 210 mmol) is dissolved in anhydrous ether (200 mL), and cooled in an ice/water bath. Acetic formic anhydride (prepared as a mixture as described above) is added dropwise. When the addition is finished, the reaction mixture is allowed to warm to RT and stirred at RT overnight. Most volatiles are removed in vacuo, and the residue solvents are removed by co-evaporation with toluene (100 mL×4). The red oil obtained precipitates upon scratching in ether, and the resulting solids are recrystallized in ether to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3) 8.32 (1H, s), 7.26 (1H, s), 6.46 (1H, bs), 5.56 (1H, d, J 7.8), 4.39 (2H, q), 1.37 (3H, t).

Workup

  1. temperaturecooled in an ice/water bath
  2. additionis added dropwise
  3. additionWhen the addition
  4. customMost volatiles are removed in vacuo
  5. customthe residue solvents are removed by co-evaporation with toluene (100 mL×4)
  6. customThe red oil obtained
  7. customprecipitates
  8. customthe resulting solids are recrystallized in ether

Sources & evidence

ORD record
ord-572de257db494463bbdbf9584753597d
Source dataset
uspto-grants-2011_08
Patent number
US08003656B2

Reaction notes

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