Sodium Carbonate → N-({9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)-2-methyl-1-propanesulfonamide

HRID 1700086Notes

Reaction equation

HRID 1700086 reaction equation
C([O:4][C@H:5]1[C@@H:9]([O:10]C(=O)C)[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([CH2:38][NH:39][S:40]([CH2:43][CH:44]([CH3:46])[CH3:45])(=[O:42])=[O:41])=[N:18][C:19]=3[NH:23][CH2:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:7][C@@H:6]1[CH2:47][O:48]C(=O)C)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>O.CO>[NH3:14].[OH:10][C@@H:9]1[C@H:5]([OH:4])[C@@H:6]([CH2:47][OH:48])[O:7][C@H:8]1[N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][C:17]([CH2:38][NH:39][S:40]([CH2:43][CH:44]([CH3:46])[CH3:45])(=[O:41])=[O:42])=[N:18][C:19]=2[NH:23][CH2:24][CH:25]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 69972041(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy) methyl]-5-(6-[(2,2-diphenylethyl)amino]-2-{[(isobutylsulfonyl)amino]methyl}-9H-purin-9-yl)tetrahydro-3-furanyl acetate

Product 2

HCID 222AmmoniaHCID 9960269N-({9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)-2-methyl-1-propanesulfonamideYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy) methyl]-5-(6-[(2,2-diphenylethyl)amino]-2-{[(isobutylsulfonyl)amino]methyl}-9H-purin-9-yl)tetrahydro-3-furanyl acetate (188 mg, 0.26 mmol) (Preparation 9) and sodium carbonate (140 mg, 1.32 mmol) in a mixture of water (2 ml) and methanol (10 ml) was stirred at room temperature for 6 hours. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and brine. The organic phase was separated and the solvent removed under reduced pressure. The residue was then purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:0.88 ammonia (95:5:0.5 by volume) gradually changing to dichloromethane:methanol:0.88 ammonia (90:10:1 by volume) to afford the title compound (77 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and brine
  3. customThe organic phase was separated
  4. customthe solvent removed under reduced pressure
  5. customThe residue was then purified by column chromatography on silica gel eluting with a gradient system of dichloromethane

Sources & evidence

ORD record
ord-8846c666b85745a8b719f1a597c2de03
Source dataset
uspto-grants-2002_02
Patent number
US06350735B1

Reaction notes

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