Hydrochloric Acid → HCID 67193749, compound

HRID 2401323Notes

Reaction equation

HRID 2401323 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][NH:6][C:7]1[N:8]([CH2:22][CH2:23][CH3:24])[C:9](=[O:21])[C:10]2[NH:11][C:12]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[N:13][C:14]=2[N:15]=1)C.C1COCC1.[OH-].[Na+].Cl>O.C(O)C>[CH:16]1([C:12]2[NH:11][C:10]3[C:9](=[O:21])[N:8]([CH2:22][CH2:23][CH3:24])[C:7]([NH:6][CH2:5][C:4]([OH:25])=[O:3])=[N:15][C:14]=3[N:13]=2)[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67194729HCID 67194729, compound

Product 1

HCID 67193749HCID 67193749, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of (8-cyclopentyl-6-oxo-1-propyl-6,7-dihydro-1H-purin-2-ylamino)-acetic acid ethyl ester (0.05 g, 0.144 mmol) prepared in the previous step in a mixture of water (5 ml), THF (5 ml) and ethanol (5 ml) was added sodium hydroxide (0.017 g, 0.425 mmol) and the resulting reaction mixture was heated at 50-60° C. overnight. The solvent was evaporated under reduced pressure and the residue was dissolved in 2 ml of water. The solution obtained was neutralized with 1N HCl. The solid formed was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous sodium sulphate and concentrated under vacuum. The crude product was purified by crystallization with dichloromethane/ether/methanol mixture to give the product (0.006 g, 13%) as a pale yellow solid.

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in 2 ml of water
  4. customThe solution obtained
  5. customThe solid formed
  6. extractionwas extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with water
  8. dry with materialdried over anhydrous sodium sulphate
  9. concentrationconcentrated under vacuum
  10. customThe crude product was purified by crystallization with dichloromethane/ether/methanol mixture

Sources & evidence

ORD record
ord-f2b6d31d0b884782920aa5a8325af940
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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