Sodium Carbonate → 6-[(2,2-Diphenylethyl)amino]-9-[(2R,3R,4S,5R)-5-(2-ethyl-2H-tetrazol-5-yl)-3,4-dihydroxytetrahydro-2-furanyl]-N-[2-(1-piperidinyl)ethyl]-9H-purine-2-carboxamide

HRID 1168275Notes

Reaction equation

HRID 1168275 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([C:45]([NH:47][CH2:48][CH2:49][N:50]1[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]1)=[O:46])=[N:25][C:26]=2[NH:30][CH2:31][CH:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[C:33]1([CH:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:31][NH:30][C:26]2[N:25]=[C:24]([C:45]([NH:47][CH2:48][CH2:49][N:50]3[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]3)=[O:46])[N:23]=[C:22]3[C:27]=2[N:28]=[CH:29][N:21]3[C@H:6]2[C@H:5]([OH:4])[C@H:9]([OH:10])[C@@H:8]([C:14]3[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=3)[O:7]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 70023610(2R,3R,4R,5R)-4-(Acetyloxy)-2-[6-[(2,2-diphenylethyl)amino]-2-({[2-(1-piperidinyl)ethyl]amino}carbonyl)-9H-purin-9-yl]-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl acetate

Product 1

HCID 590945016-[(2,2-Diphenylethyl)amino]-9-[(2R,3R,4S,5R)-5-(2-ethyl-2H-tetrazol-5-yl)-3,4-dihydroxytetrahydro-2-furanyl]-N-[2-(1-piperidinyl)ethyl]-9H-purine-2-carboxamideYield 76.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of (2R,3R,4R,5R)-4-(acetyloxy)-2-[6-[(2,2-diphenylethyl)amino]-2-({[2-(1-piperidinyl)ethyl]amino}carbonyl)-9H-purin-9-yl]-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl acetate (Preparation 27) (230 mg, 0.31 mmol) and sodium carbonate (130 mg, 1.23 mmol) in methanol (15 ml) and water (1.5 ml) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was partioned between ethyl acetate (50 ml) and water (10 ml). The organic layer was washed with brine (10 ml), dried (anhydrous sodium sulphate) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume) gradually changing to dichloromethane:methanol:0.88 concentrated aqueous ammonia (93:7:0.7 by volume). Product containing fractions were evaporated and the resulting solid triturated with ether, filtered and dried to afford the title compound as a white powder (158 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washThe organic layer was washed with brine (10 ml)
  3. dry with materialdried (anhydrous sodium sulphate)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane
  6. additionProduct containing fractions
  7. customwere evaporated
  8. customthe resulting solid triturated with ether
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-e0da28a2fc224433beca0f87ecd46817
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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