Hydrochloric Acid → 2-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]-3-phenylpropanoic acid

HRID 1534958Notes

Reaction equation

HRID 1534958 reaction equation
[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([NH:15][CH:16]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:17]([O:19]C)=[O:18])=[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]([NH:15][CH:16]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:17]([OH:19])=[O:18])=[O:14])[CH:5]=[N:4][C:3]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 1364033592-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]-3-phenylpropanoic acid, methyl ester

Product 1

HCID 1364033582-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]-3-phenylpropanoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 mg (0.271 mmol) of 2-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]-3-phenylpropanoic acid, methyl ester (AIT-0085) were placed into a 10 ml beaker equipped with a magnetic stirring bar. Water (5 ml) was added to the beaker and stirring was started. To the stirring heterogeneous mixture was added 100 mg (1.79 mmol) of KOH pellets. Within a few seconds the reaction mixture became a homogeneous green color. Stirring was continued for one hour. The pH of the solution was adjusted to 2.0 with concentrated hydrochloric acid. The product was collected by vacuum filtration and washed twice with 2 ml of water and then twice with 2 ml of acetone. The weight of the product, 2-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)1-oxopropyl]amino]-3-phenylpropanoic acid (AIT-0086), was 80 mg. Yield: 83%. m.p. 240°-242° C.

Workup

  1. custombeaker equipped with a magnetic stirring bar
  2. waitWithin a few seconds the reaction mixture became
  3. stirringStirring
  4. filtrationThe product was collected by vacuum filtration
  5. washwashed twice with 2 ml of water

Sources & evidence

ORD record
ord-8a9b19332cde42b99ef7e70be7320abd
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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