Glycine, N-formyl-, ethyl ester → N-((3-Cyclopropyl-1,2,4-oxadiazol-5-yl)methyl)formamide

HRID 623186

Reaction equation

HRID 623186 reaction equation
[CH:1]([NH:3][CH2:4][C:5]([O:7]CC)=O)=[O:2].[CH:10]1([C:13](=[N:15]O)[NH2:14])[CH2:12][CH2:11]1>CCO>[CH:10]1([C:13]2[N:15]=[C:5]([CH2:4][NH:3][CH:1]=[O:2])[O:7][N:14]=2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 76615Glycine, N-formyl-, ethyl esterHCID 2794666N'-Hydroxycyclopropanecarboximidamide

Product 1

HCID 14460538N-((3-Cyclopropyl-1,2,4-oxadiazol-5-yl)methyl)formamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl formylaminomethyl-carboxylate (150 mmol) and cyclopropyl carboxamide oxime (100 mmol) in 100% EtOH (100 ml) was charged with Na (200 mg) and crushed molecular sieve (4 Å) (10 g). The mixture thus obtained was stirred and heated to reflux for 16 hours. The mixture was cooled to room temperature, filtered through filter aid and the filtrate was evaporated in vacuo. The oily residue was partitioned into a CHCl3 phase which was dried with Na2SO4 and evaporated to give the title compound as an oil.

Workup

  1. customcrushed molecular sieve (4 Å) (10 g)
  2. customThe mixture thus obtained
  3. temperatureheated
  4. temperatureto reflux for 16 hours
  5. filtrationfiltered
  6. filtrationthrough filter aid
  7. customthe filtrate was evaporated in vacuo
  8. customThe oily residue was partitioned into a CHCl3 phase which
  9. dry with materialwas dried with Na2SO4
  10. customevaporated

Sources & evidence

ORD record
ord-2a36dc4819874c6a8f7da88605dcdeed
Source dataset
uspto-grants-1988_09
Patent number
US04774245

Linked notes

Loading…