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 10441

Reaction equation

HRID 10441 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 98%

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 8) (3.4 g, 4.5 mmol) and sodium carbonate (50 mg) in dry methanol (60 ml) was stirred at room temperature for four hours. Solvent was removed under reduced pressure and the residue taken up in a mixture of dichloromethane:methanol (95:5, by volume, 60 ml). Inorganic salts were filtered off and the filtrate evaporated under reduced pressure. The residue was triturated with diethyl ether, filtered off and dried to yield the title compound as a white solid, (2.4 g, 98%).

Workup

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

Sources & evidence

ORD record
ord-5ad4245a898440bbbc97f5b29c144228
Source dataset
uspto-grants-2006_08
Patent number
US07094769B2

Linked notes

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