Potassium Carbonate → HCID 9895687, compound

HRID 1060541Notes

Reaction equation

HRID 1060541 reaction equation
C([O:9][C@@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@@H:13]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])[O:12][C@H:11]1[N:29]1[CH:37]=[N:36][C:35]2[C:30]1=[N:31][C:32]([C:53]([NH:55][CH2:56][CH2:57][N:58]1[CH2:63][CH2:62][CH2:61][CH2:60][CH2:59]1)=[O:54])=[N:33][C:34]=2[NH:38][CH2:39][CH:40]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:47]1([CH:40]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:39][NH:38][C:34]2[N:33]=[C:32]([C:53]([NH:55][CH2:56][CH2:57][N:58]3[CH2:63][CH2:62][CH2:61][CH2:60][CH2:59]3)=[O:54])[N:31]=[C:30]3[C:35]=2[N:36]=[CH:37][N:29]3[C@H:11]2[C@H:10]([OH:9])[C@H:14]([OH:15])[C@@H:13]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])[O:12]2)[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69543872HCID 69543872, compound

Product 1

HCID 9895687HCID 9895687, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2R,3R,4R,5S)-4-(benzoyloxy)-2-[6-[(2,2-diphenylethyl)amino]-2-({[2-(1-piperidinyl)-ethyl]amino}carbonyl)-9H-purin-9-yl]-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate (Preparation 7) (104 mg, 0.12 mmol) in methanol (3 ml) was treated with potassium carbonate (100 mg, 0.72 mmol). The mixture was stirred at room temperature for 30 minutes. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried with anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane: methanol (90:10 by volume) to afford the title compound as a white solid (44 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried with anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane: methanol (90:10 by volume)

Sources & evidence

ORD record
ord-28f85b657dde4acabd7db7025122f693
Source dataset
uspto-grants-2003_02
Patent number
US06525032B2

Reaction notes

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