Sodium Carbonate → (2S,3S,4R,5R)-5-{6-[(2-Benzyl-3-phenylpropyl)amino]-2-iodo-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide

HRID 1060560Notes

Reaction equation

HRID 1060560 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]([I:55])=[N:33][C:34]=2[NH:38][CH2:39][CH:40]([CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH2:48]([CH:40]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:39][NH:38][C:34]1[N:33]=[C:32]([I:55])[N:31]=[C:30]2[C:35]=1[N:36]=[CH:37][N:29]2[C@@H:11]1[O:12][C@H:13]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])[C@@H:14]([OH:15])[C@H:10]1[OH:9])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 10212972(2R,3R,4S, 5S)-4-(Benzoyloxy)-2-{6-[(2-benzyl-3-phenylpropyl)amino]-2-iodo-9H-purin-9-yl}-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate

Product 1

HCID 10211562(2S,3S,4R,5R)-5-{6-[(2-Benzyl-3-phenylpropyl)amino]-2-iodo-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamideYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2R,3R,4S,5S)-4-(benzoyloxy)-2-{6-[(2-benzyl-3-phenylpropyl)amino)-2-iodo-9H-purin-9-yl}-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate (Preparation 20) (0.26 g, 0.31 mmol) and sodium carbonate (33 mg, 0.3 mmol) in methanol (5 ml) was stirred at room temperature for 14 hours. Solvent was removed under reduced pressure and the residue dissolved in dichloromethane:methanol (99:1 by volume; 5 ml) and filtered. Solvent was again evaporated under reduced pressure and the residue triturated with diethyl ether to afford the title compound as a beige powder (0.17 g, 86%).

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane:methanol (99:1 by volume; 5 ml)
  3. filtrationfiltered
  4. customSolvent was again evaporated under reduced pressure
  5. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-9aeb8480367f46278b947d4ae247889e
Source dataset
uspto-grants-2003_02
Patent number
US06525032B2

Reaction notes

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