HCID 11962692, compound → HCID 11962695, compound

HRID 130308Notes

Reaction equation

HRID 130308 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][CH:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:25]1[CH:29]=[C:28]([C:30]([O:32]CC)=[O:31])[N:27]=[N:26]1)=[N:14][C:15]=2[NH:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>[OH-].[K+].CO>[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][CH:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:25]1[CH:29]=[C:28]([C:30]([OH:32])=[O:31])[N:27]=[N:26]1)=[N:14][C:15]=2[NH:19][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

4

Reactant 1

HCID 11962692HCID 11962692, compound

Product 1

HCID 11962695HCID 11962695, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

100 mg of the ethyl 1-{9-[(4S,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(cyclopentylamino)purin-2-yl}-1,2,3-triazole-4-carboxylate prepared in Example 4A was dissolved in approximately 10 mL of 1 N KOH in methanol. The solution was stirred at 60° C. for 24 hours. The solvent was then removed and the residue dissolved in 5 mL ethyl acetate. The aqueous phase was brought to a pH of 3-4 by addition of 37% HCL. The resulting solid was collected by filtration and washed with water and ether then air dried to provide the product, 1-{9-[(4S,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(cyclopentylamino)purin-2-yl}-1,2,3-triazole-4-carboxylic acid.

Workup

  1. customThe solvent was then removed
  2. dissolutionthe residue dissolved in 5 mL ethyl acetate
  3. additionThe aqueous phase was brought to a pH of 3-4 by addition of 37% HCL
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water and ether
  6. customair dried

Sources & evidence

ORD record
ord-cbde697a4ed2475fb894d90b45e5a6cf
Source dataset
uspto-grants-2008_06
Patent number
US07381714B2

Reaction notes

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