Glycine ethyl ester → Ethyl N-(2-amino-3-methyl-5-[1,2,4-triazol-1-yl]benzyl)glycinate

HRID 2231654Notes

Reaction equation

HRID 2231654 reaction equation
[NH2:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)=[CH:11][C:10]=1[CH:21]=O>C(Cl)(Cl)Cl>[NH2:8][C:9]1[C:10]([CH3:21])=[CH:11][C:12]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)=[CH:13][C:14]=1[CH2:15][NH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 12176Glycine ethyl esterHCID 212855331-(4-Amino-3-formyl-5-methylphenyl)-1,2,4-triazole

Product 1

HCID 21285535Ethyl N-(2-amino-3-methyl-5-[1,2,4-triazol-1-yl]benzyl)glycinateYield 51.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of ethyl glycinate (0.38 g), 1-(4-amino-3-formyl-5-methylphenyl)-1,2,4-triazole (0.5 g) and 3Å molecular sieves (1.0 g; "Fluka" [Trade Mark] article No. 69828) was stirred and heated under reflux in chloroform (10 cm3) for 4 hours. The cooled mixture was filtered, evaporated in vacuo, and the residue taken into ethanol (30 cm3). The solution was then hydrogenated at 60 p.s.i. (4.13×105Pa) pressure and room temperature (20°) over 10% palladised charcoal (0.2 g) for 16 hours. The catalyst was then removed by filtration through "Solkafloc" (Trade Mark) and the solution was evaporated in vacuo to give an oil which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with chloroform. Combination and evaporation of the appropriate fractions afforded the title compound as an oil (0.37 g).

Workup

  1. temperatureheated
  2. filtrationThe cooled mixture was filtered
  3. customevaporated in vacuo
  4. customThe catalyst was then removed by filtration through "Solkafloc" (Trade Mark)
  5. customthe solution was evaporated in vacuo
  6. customto give an oil which
  7. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  8. washeluting with chloroform
  9. customCombination and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-5e2319d83dd4442793c8033c90c3376d
Source dataset
uspto-grants-1988_11
Patent number
US04783467

Reaction notes

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