Sodium Hydroxide → HCID 67193289, compound

HRID 2401318Notes

Reaction equation

HRID 2401318 reaction equation
C([O:3][C:4](=[O:34])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[N:13]([CH2:31][CH2:32][CH3:33])[C:14](=[O:30])[C:15]3[NH:16][C:17]([C:21]45[CH2:28][CH:27]6[CH2:29][CH:23]([CH2:24][CH:25]4[CH2:26]6)[CH2:22]5)=[N:18][C:19]=3[N:20]=2)[CH:6]=1)C.[OH-].[Na+]>C(O)C.C1COCC1>[CH2:24]1[CH:25]2[C:21]3([C:17]4[NH:16][C:15]5[C:14](=[O:30])[N:13]([CH2:31][CH2:32][CH3:33])[C:12]([O:11][C:7]6[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=6)[C:4]([OH:34])=[O:3])=[N:20][C:19]=5[N:18]=4)[CH2:28][CH:27]([CH2:29][CH:23]1[CH2:22]3)[CH2:26]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67204002HCID 67204002, compound

Product 1

HCID 67193289HCID 67193289, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-[8-(Hexahydro-2,5-methano-pentalen-3a-yl)-6-oxo-1-propyl-6,7-dihydro-1H-purin-2-yloxy]-benzoic acid ethyl ester (prepared by following similar, procedure as Example 1, 0.073 g, 0.157 mmol) in a mixture of ethanol (5 ml) water (5 ml) and THF (5 ml) was added sodium hydroxide (0.019 g, 0.473 mmol) and the reaction mixture was heated at 50° C. overnight. The reaction mixture after cooling to room temperature was concentrated under vacuum to remove THF. The aqueous layer was acidified with 1N HCl. The precipitate obtained was extracted with ethylacetate. The ethyl acetate layer was dried over anhydrous sodium sulphate and concentrated under vacuum. The crude product was purified by column chromatography using 5% methanol in DCM as the eluant to give the product (0.041 g, 59%) as an off white solid.

Workup

  1. temperatureThe reaction mixture after cooling to room temperature
  2. concentrationwas concentrated under vacuum
  3. customto remove THF
  4. customThe precipitate obtained
  5. extractionwas extracted with ethylacetate
  6. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulphate
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-d80ac2e6245746ffbdb69ee7943a8666
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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