Dimethyl Sulfoxide → 2-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]-3-phenylpropanoic acid, methyl ester

HRID 1534957Notes

Reaction equation

HRID 1534957 reaction equation
[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([O:15]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH:5]=[N:4][C:3]1=2.Cl.[CH3:26][O:27][C:28](=[O:38])[C@H:29]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[NH2:30].CS(C)=O.C(N(CC)CC)C>C(#N)C>[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([NH:30][CH:29]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:28]([O:27][CH3:26])=[O:38])=[O:15])[CH:5]=[N:4][C:3]1=2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 1359739573-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester

Product 1

HCID 1364033592-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]-3-phenylpropanoic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.500 g (1.519 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester (AIT-0081) and 0.328 g (1.519 mmol) of L-phenylalanine methyl ester hydrochloride were placed in a 25 ml round bottom flask equipped with a magnetic stirring bar. 3 ml of dimethylsulfoxide was added and the solution was stirred to dissolve as much solid as possible at room temperature. Then 159 mg (1.571 mmol) of triethylamine was added and the solution was stirred at room temperature (20° C.) for one hour. 10 ml of acetonitrile was added to the stirring solution. The solution was triturated with ether until a white precipitate had formed. The solution was filtered to remove the triethylamine hydrochloride. The mother liquor was again treated with ether to produce a precipitate. The mixture was filtered and the white solid was washed with ethyl ether and dried. This yielded 0.465 g of a white solid. The white solid material was added to 22 ml ethanol/H2O 9:1 and was heated to dissolve the compound. After allowing to cool to room temperature, ether was added until just before the cloud point. The solution was placed in a refrigerator overnight. Upon filtration and washing with ether, 0.235 g of 2-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]-3-phenylpropanoic acid, methyl ester (AIT-0085) as a white crystalline material was obtained. m.p. 186°-191° C.

Workup

  1. customequipped with a magnetic stirring bar
  2. dissolutionto dissolve as much solid as possible at room temperature
  3. stirringthe solution was stirred at room temperature (20° C.) for one hour
  4. customThe solution was triturated with ether until a white precipitate
  5. customhad formed
  6. filtrationThe solution was filtered
  7. customto remove the triethylamine hydrochloride
  8. additionThe mother liquor was again treated with ether
  9. customto produce a precipitate
  10. filtrationThe mixture was filtered
  11. washthe white solid was washed with ethyl ether
  12. customdried
  13. additionThe white solid material was added to 22 ml ethanol/H2O 9:1
  14. temperaturewas heated
  15. dissolutionto dissolve the compound
  16. additionether was added until just before the cloud point
  17. customwas placed in a refrigerator overnight
  18. filtrationUpon filtration
  19. washwashing with ether, 0.235 g of 2-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]-3-phenylpropanoic acid, methyl ester (AIT-0085) as a white crystalline material
  20. customwas obtained

Sources & evidence

ORD record
ord-fabc3432d70541d593ba29cd63c6db54
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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