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2,2-Dimethoxypropane → N6-benzoyl-2',3'-isopropylidene adenosine

HRID 552719
Notes
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Reaction equation

HRID 552719 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][CH:13]=[N:14][C:15]=2[NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CO[C:30](OC)([CH3:32])[CH3:31].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CC(C)=O>[OH:9][CH2:8][C@@H:5]1[C@H:6]2[O:7][C:30]([CH3:32])([CH3:31])[O:1][C@H:2]2[C@H:3]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:19][C:20](=[O:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[O:4]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 64952,2-DimethoxypropaneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 11728391N6-Benzoyladenosine

Product 1

HCID 10001645N6-benzoyl-2',3'-isopropylidene adenosineYield 59%

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent

Procedure

N-{9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-9H-purin-6-yl}benzamide (0.643 g, 1.73 mmol), 2,2-dimethoxypropane (1.06 mL, 8.66 mmol), and para-toluenesulfonic acid monohydrate (0.333 g, 1.73 mmol) were dissolved in acetone (43 mL). The solution was stirred at room temperature overnight and then heated to 40° C. for 3 hours. Once cooled to room temperature, saturated sodium bicarbonate solution was added to the reaction mixture and then approximately half the solvent was removed in vacuo. The resulting solution was diluted with water and extracted four times with CH2Cl2. Combined organics were washed with brine and dried over Na2SO4. The crude material was purified by silica gel chromatography (0 to 5% MeOH/CH2Cl2) to isolate the title compound (0.419 g, 59%)

Workup

  1. temperatureheated to 40° C. for 3 hours
  2. temperatureOnce cooled to room temperature
  3. customapproximately half the solvent was removed in vacuo
  4. additionThe resulting solution was diluted with water
  5. extractionextracted four times with CH2Cl2
  6. washCombined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. customThe crude material was purified by silica gel chromatography (0 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-fb48fd8290eb48d1bdd1f3c77947b513
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07951810B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes