Potassium Hydroxide → HCID 57629182, compound

HRID 2108346Notes

Reaction equation

HRID 2108346 reaction equation
[CH3:1][Si:2]([CH3:55])([O:7][C@@H:8]1[C@H:12]([O:13][Si:14]([CH3:20])([CH3:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[C@@H:11]([CH2:21][O:22][Si:23]([CH3:29])([CH3:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[O:10][C@H:9]1[N:30]1[CH:38]=[N:37][C:36]2[C:31]1=[N:32][C:33]([N:45]1[CH:49]=[C:48]([C:50]([O:52]CC)=[O:51])[CH:47]=[N:46]1)=[N:34][C:35]=2[NH:39][CH:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1)[C:3]([CH3:6])([CH3:5])[CH3:4].[OH-].[K+]>C(O)C>[CH3:55][Si:2]([CH3:1])([O:7][C@@H:8]1[C@H:12]([O:13][Si:14]([CH3:20])([CH3:19])[C:15]([CH3:16])([CH3:17])[CH3:18])[C@@H:11]([CH2:21][O:22][Si:23]([CH3:28])([CH3:29])[C:24]([CH3:27])([CH3:26])[CH3:25])[O:10][C@H:9]1[N:30]1[CH:38]=[N:37][C:36]2[C:31]1=[N:32][C:33]([N:45]1[CH:49]=[C:48]([C:50]([OH:52])=[O:51])[CH:47]=[N:46]1)=[N:34][C:35]=2[NH:39][CH:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1)[C:3]([CH3:4])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57629186HCID 57629186, compound

Product 1

HCID 57629182HCID 57629182, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.75 g of ethyl 1-(9-{(2R,3R,4R,5R)-3,4-bis(1,1,2,2-tetramethyl-1-silapropoxy)-5-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]oxolan-2-yl}-6-(cyclopentylamino)purin-2-yl)pyrazole-4-carboxylate prepared as described in Example 11A and 0.5 g KOH were stirred in 50 mL of ethanol at room temperature overnight. In the morning the mixture was refluxed for 1.5 hours. After reflux, the product was concentrated and the residue dissolved in 30 mL of water and acidified to a pH of 2.0 using a 2N aqueous HCl solution. The product was then extracted with ethyl acetate and the combined organic layers were dried over Na2SO4. The solvent was removed by evaporation and the product purified using a graduated, 2:3 to 3:2 ethyl acetate/hexane column to provide 1-(9-{(2R,3R,4R,5R)-3,4-bis(1,1,2,2-tetramethyl-1-silapropoxy)-5-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]oxolan-2-yl}-6-(cyclopentylamino)purin-2-yl)pyrazole-4-carboxylic acid.

Workup

  1. temperatureIn the morning the mixture was refluxed for 1.5 hours
  2. temperatureAfter reflux
  3. concentrationthe product was concentrated
  4. dissolutionthe residue dissolved in 30 mL of water
  5. extractionThe product was then extracted with ethyl acetate
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. customThe solvent was removed by evaporation
  8. customthe product purified

Sources & evidence

ORD record
ord-ec2756a1b54e4a15ae764595d6ebfbea
Source dataset
uspto-grants-2009_04
Patent number
US07514417B2

Reaction notes

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