Dicyclohexylcarbodiimide → HCID 136020866, compound

HRID 1534967Notes

Reaction equation

HRID 1534967 reaction equation
[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[N:4][C:3]1=2.C1(N=C=NC2CCCCC2)CCCCC1.CN(C)C(=O)C.[CH3:37][N:38]([CH3:43])[CH2:39][CH:40](O)[CH3:41]>CCOCC.CC(C)=O>[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([O:15][CH:40]([CH3:41])[CH2:39][N:38]([CH3:43])[CH3:37])=[O:14])[CH:5]=[N:4][C:3]1=2

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 31374DimethylacetamideHCID 37511DimepranolHCID 1354540023-(6-Oxo-3,6-dihydro-9h-purin-9-yl)propanoic acid

Product 1

HCID 136020866HCID 136020866, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

0.300 g (1.441 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid (AIT-0080) and 0.305 g (1.478 mmol) of dicyclohexylcarbodiimide were placed into a 10 ml round bottom flask equipped with magnetic stirring bar and thermometer. 4 ml of N,N-dimethylacetamide and 0.168 g (1.628 mmol) of 1-dimethyamino-2-propanol were added and the solution was heated to 75° (closed flask) for two hours. The solution was allowed to come to room temperature and a large amount of precipitate formed. The contents were transferred to a larger flask with 20 ml of acetone. 20 ml of ether was added and the solution was allowed to cool down in the refrigerator. Crystals formed within a short period of time. A solid was obtained by filtration and washed with ether. 408 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 1-(dimethylamino)-2-propyl ester (AIT-0106) as a white crystalline solid was obtained. Yield: 97%. m.p.: 280° -284°.

Workup

  1. customequipped with magnetic stirring bar
  2. temperaturethe solution was heated to 75°
  3. custom(closed flask) for two hours
  4. customto come to room temperature
  5. customa large amount of precipitate formed
  6. temperatureto cool down in the refrigerator
  7. customCrystals formed within a short period of time
  8. customA solid was obtained by filtration
  9. washwashed with ether

Sources & evidence

ORD record
ord-f45cc8e5d14e4aaeae8e50e854bcdeaa
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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