Acetic Acid → Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

HRID 1534927Notes

Reaction equation

HRID 1534927 reaction equation
N[CH:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[N:4][C:3]1=2.C(O)(=[O:20])C.N([O-])=O.[Na+]>O>[O:20]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[N:4][C:3]1=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23668193Sodium NitriteHCID 178471844HCID 178471844, compound

Product 1

HCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoateYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

3-(1.6-dihydro-6-amino-9H-purin-9-yl)propionic acid, ethyl ester (15.2 g., 64.6 mmol) (AIT-0026) was placed into a 500 ml round bottom flask with 350 ml glacial acetic acid and was stirred to complete dissolution. While stirring, 22.3 g (0.323 mol) NaNO2 dissolved in water (saturated) was added dropwise over a period of one hour using a dropping funnel (pressure equalizing). A brown gas formed during the addition. The flask was stoppered shortly after the addition was complete and the solution was stirred at room temperature for 24 hours. The solvent was removed under reduced pressure (approximately 45°-50° C.). The residue was washed with cold (0° C.) absolute ethanol and filtered. The resulting white solid was dissolved in 175 ml ethanol/water (70/30) and was cooled to 0° C. overnight. The resulting precipitate was obtained by filtration. The solid was placed into a flask with a magnetic stirring bar and was washed with water by vigorous stirring. The solution was filtered by Buchner vacuum filtration and the resulting white solid was dried in vacuo at 50° C. to yield 4.6 g (19.5 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027). Yield: 30%.

Workup

  1. stirringWhile stirring
  2. additionwas added dropwise over a period of one hour
  3. customA brown gas formed during the addition
  4. additionafter the addition
  5. stirringthe solution was stirred at room temperature for 24 hours
  6. customThe solvent was removed under reduced pressure (approximately 45°-50° C.)
  7. washThe residue was washed with cold (0° C.) absolute ethanol
  8. filtrationfiltered
  9. dissolutionThe resulting white solid was dissolved in 175 ml ethanol/water (70/30)
  10. customThe resulting precipitate was obtained by filtration
  11. customThe solid was placed into a flask with a magnetic stirring bar
  12. washwas washed with water by vigorous stirring
  13. filtrationThe solution was filtered by Buchner vacuum filtration
  14. customthe resulting white solid was dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-70433da9a5534f48b8a2ff6c8cdb7808
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

Loading…