Acetone → (2S,3S,4R,5R)-5-(6-[(2,2-Diphenylethyl)amino]-2-{[({[2-(1-piperidinyl)ethyl]amino}carbonyl)amino]methyl}-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide

HRID 897075Notes

Reaction equation

HRID 897075 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:15][C@H:16]1[C@@H:20]([O:21]C(=O)C2C=CC=CC=2)[C@H:19]([N:30]2[CH:38]=[N:37][C:36]3[C:31]2=[N:32][C:33]([CH2:54][NH:55][C:56]([NH:58][CH2:59][CH2:60][N:61]2[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]2)=[O:57])=[N:34][C:35]=3[NH:39][CH2:40][CH:41]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:18][C@@H:17]1[C:67]([NH:69][CH2:70][CH3:71])=[O:68])(=O)C1C=CC=CC=1.CC(C)=O>CO>[C:42]1([CH:41]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH2:40][NH:39][C:35]2[N:34]=[C:33]([CH2:54][NH:55][C:56]([NH:58][CH2:59][CH2:60][N:61]3[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]3)=[O:57])[N:32]=[C:31]3[C:36]=2[N:37]=[CH:38][N:30]3[C@@H:19]2[O:18][C@H:17]([C:67]([NH:69][CH2:70][CH3:71])=[O:68])[C@@H:16]([OH:15])[C@H:20]2[OH:21])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 11430Potassium Carbonate2×HCID 58904390(2S,3S,4R,5R)-4-(Benzoyloxy)-5-(6-[(2,2-diphenylethyl)amino]-2-{[({[2-(1-piperidinyl) ethyl]amino}carbonyl)amino]methyl}-9H-Purin-9-yl)-2-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate

Product 1

HCID 10305241(2S,3S,4R,5R)-5-(6-[(2,2-Diphenylethyl)amino]-2-{[({[2-(1-piperidinyl)ethyl]amino}carbonyl)amino]methyl}-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamideYield 19.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (20 mg, 0.14 mmol) was added to a solution of (2S,3S,4R,5R)-4-(benzoyloxy)-5-(6-[(2,2-diphenylethyl)amino]-2-{[({[2-(1-piperidinyl)ethyl]amino}carbonyl)amino]methyl}-9H-purin-9-yl)-2-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate (100 mg, 0.13 mmol) (Preparation 14) in methanol (100 ml). The reaction mixture was stirred at room temperature for 2 hours. More potassium carbonate (20 mg, 0.14 mmol) was then added and the reaction mixture was heated to 60° C. for 2 hours. The solvent was removed under reduced pressure to give a residue that was slurried with acetone and filtered. The filtrate was evaporated under reduced pressure and the residue was partially purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (90:10:1 by volume). The residue after solvent evaporation under reduced pressure was repurified by more column chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (90:10:1 by volume). The solvent was removed by evaporation under reduced pressure to give the title compound as a foam (17 mg).

Workup

  1. temperaturethe reaction mixture was heated to 60° C. for 2 hours
  2. customThe solvent was removed under reduced pressure
  3. customto give a residue that
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. customthe residue was partially purified by column chromatography on silica gel eluting with dichloromethane
  7. customThe residue after solvent evaporation under reduced pressure
  8. customwas repurified by more column chromatography on silica gel eluting with dichloromethane
  9. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-9f74dbb77ee84360b5cce84545194b90
Source dataset
uspto-grants-2005_07
Patent number
US06921753B2

Reaction notes

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