Water → (2R,3R,4S,5R)-2-{2-[(Benzylsulfonyl)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268371Notes

Reaction equation

HRID 2268371 reaction equation
[CH2:1]([S:8][CH2:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[C@H:19]2[C@H:23]([OH:24])[C@H:22]([OH:25])[C@@H:21]([CH2:26][O:27][CH3:28])[O:20]2)=[C:12]([NH:29][CH2:30][CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[OH:45].[Na+].OOS([O-])=O.[K+].ClCCl.[OH2:58]>CC(C)=O.C(OCC)(=O)C>[CH2:1]([S:8]([CH2:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[C@H:19]2[C@H:23]([OH:24])[C@H:22]([OH:25])[C@@H:21]([CH2:26][O:27][CH3:28])[O:20]2)=[C:12]([NH:29][CH2:30][CH:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:11]=1)(=[O:45])=[O:58])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 962Water2×HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 59975291(2R,3R,4S,5R)-2-{2-[(Benzylsulfanyl)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

Product 1

HCID 9809405(2R,3R,4S,5R)-2-{2-[(Benzylsulfonyl)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2R,3R,4S,5R)-2-{2-[(Benzylsulfanyl)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (100 mg, 0.17 mmol) (example 76) was dissolved in stirred acetone (3 ml) and solid sodium hydrogen carbonate (100 mg, 1.2 mmol) added. A solution of Oxone (trade mark) (potassium peroxymonosulphate) (410 mg, 0.68 mmol) dissolved in water (2 ml) was then added dropwise to the original solution over the course of 30 min. Dichloromethane (2 ml) was also added and the reaction mixture stirred at room temperature for 60 hr. The reaction mixture was then diluted with ethyl acetate (100 ml) and water (50 ml). The organic layer was separated, dried with anhydrous magnesium sulfate and the solvent removed under reduced pressure to give a residue which was purified by column chromatography on silica gel eluting with a solvent gradient of ethyl acetate:hexane (4:1) increasing in polarity to ethyl acetate:methanol (96:4). This gave the title compound (50 mg) as a gum. MS: 630 (MH+).

Workup

  1. additionwas then added dropwise to the original solution over the course of 30 min
  2. customThe organic layer was separated
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customthe solvent removed under reduced pressure
  5. customto give a residue which
  6. customwas purified by column chromatography on silica gel eluting with a solvent gradient of ethyl acetate:hexane (4:1)
  7. temperatureincreasing in polarity to ethyl acetate:methanol (96:4)

Sources & evidence

ORD record
ord-42a6c80f78a14215bacd0abafd232d16
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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