Sodium Carbonate → Methyl 6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxylate

HRID 1060552

Reaction equation

HRID 1060552 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]([O:55][CH3:56])=[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-].[Na+].[Na+]>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]([O:55][CH3:56])=[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 10340Sodium CarbonateHCID 18345898methyl 9-{(2R,3R,4R,5S)-3,4-bis(benzoyloxy)-5-[(ethylamino)carbonyl]-tetrahydro-2-furanyl}-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate

Product 1

HCID 10187396Methyl 6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxylateYield 97.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 9-{(2R,3R,4R,5S)-3,4-bis(benzoyloxy)-5-[(ethylamino)carbonyl]-tetrahydro-2-furanyl}-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (Preparation 10) (3.4 g, 4.5 mmol) and sodium carbonate (50 mg) in dry methanol (60 ml) was stirred at room temperature for four hours. The solvent was removed under reduced pressure and the residue was taken up in a mixture of dichloromethane:methanol (95:5 by volume, 60 ml). Inorganic salts were filtered off and the filtrate was evaporated under reduced pressure. The residue was triturated with ether, filtered off and dried to yield the target compound as a white solid (2.4 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was taken up in a mixture of dichloromethane:methanol (95:5 by volume, 60 ml)
  3. filtrationInorganic salts were filtered off
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was triturated with ether
  6. filtrationfiltered off
  7. customdried

Sources & evidence

ORD record
ord-db61013a99524ec0ae08eedc141c61cf
Source dataset
uspto-grants-2003_02
Patent number
US06525032B2

Linked notes

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