Hydrochloric Acid → 3-(6-Oxo-3,6-dihydro-9h-purin-9-yl)propanoic acid

HRID 1534954Notes

Reaction equation

HRID 1534954 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]CC)=[O:14])[CH:5]=[N:4][C:3]1=2.[OH-].[K+].Cl>O>[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

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 1354540023-(6-Oxo-3,6-dihydro-9h-purin-9-yl)propanoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20.00 g (84.66 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, ethyl ester (AIT-0027) was placed into a 500 ml round bottom flask equipped with a magnetic stirring bar. 150 ml of water was added to the flask and the solution stirred. To the stirring heterogeneous solution was added 10.46 g (0.1854 mol) of KOH pellets. Within a few minutes the solution became a homogeneous light green color. The solution was stirred at room temperature for 3.5 hours. The solution was acidified (pH approximately 1.0) with concentrated HCl. The precipitated solution was placed at 4° C. overnight. The solid was collected by filtration, washed sequentially with water, methanol and ether, and dried. 17.63 g (84.7 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid (AIT-0080) was obtained as a free flowing white solid. Yield: 100%.

Workup

  1. customequipped with a magnetic stirring bar
  2. waitWithin a few minutes the solution became
  3. stirringThe solution was stirred at room temperature for 3.5 hours
  4. filtrationThe solid was collected by filtration
  5. washwashed sequentially with water, methanol and ether
  6. customdried

Sources & evidence

ORD record
ord-9b3cbeda135b46ca8d0e7a0c307082f8
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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