Sodium Hydroxide → HCID 67193350, compound

HRID 2401321Notes

Reaction equation

HRID 2401321 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]2[N:13]([CH2:27][CH2:28][CH3:29])[C:14](=[O:26])[C:15]3[NH:16][C:17]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:18][C:19]=3[N:20]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>CO.O.C1COCC1>[CH:21]1([C:17]2[NH:16][C:15]3[C:14](=[O:26])[N:13]([CH2:27][CH2:28][CH3:29])[C:12]([NH:11][CH2:10][C:7]4[CH:8]=[CH:9][C:4]([C:3]([OH:30])=[O:2])=[CH:5][CH:6]=4)=[N:20][C:19]=3[N:18]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67193541HCID 67193541, compound

Product 1

HCID 67193350HCID 67193350, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 4-[(8-cyclopentyl-6-oxo-1-propyl-6,7-dihydro-1H-purin-2-ylamino)-methyl]-benzoic acid methyl ester (0.081 g, 0.198 mmol) in a mixture of MeOH/H2O/THF (5 ml each) was added NaOH (0.024 g, 0.594 mmol) and the resulting reaction mixture was refluxed overnight. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water and neutralized with 1N HCl and then extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulphate and concentrated under vacuum. The crude product was purified by washing repeatedly with diethyl ether to give the product (0.025 g, 32%) as an off white solid.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water and neutralized with 1N HCl
  5. extractionextracted with ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulphate
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified
  9. washby washing repeatedly with diethyl ether

Sources & evidence

ORD record
ord-4d5cbb805c384f9eb0e056a4a5d20867
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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