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Adenine → HCID 67823190, compound

HRID 1492471
Notes
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Reaction equation

HRID 1492471 reaction equation
[H-].[Na+].[N:3]1[C:11]([NH2:12])=[C:10]2[C:6]([N:7]=[CH:8][NH:9]2)=[N:5][CH:4]=1.[C:13]([O:21][CH2:22][C@@H:23]1[C@@H:29]([CH2:30][O:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:28][CH:27]2[CH:25]([O:26]2)[CH2:24]1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.P([O-])([O-])([O-])=O>CN(C=O)C.CO>[C:32]([O:31][CH2:30][C@@H:29]1[C@@H:23]([CH2:22][O:21][C:13](=[O:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:24][C@@H:25]([N:7]2[CH:8]=[N:9][C:10]3[C:6]2=[N:5][CH:4]=[N:3][C:11]=3[NH2:12])[C@H:27]([OH:26])[CH2:28]1)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 190AdenineHCID 1061PhosphateHCID 24758Sodium hydrideHCID 15280201HCID 15280201, compound

Product 1

HCID 67823190HCID 67823190, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 6228DimethylformamideSolvent

Procedure

In an atmosphere of argon gas, 60% sodium hydride (20 mg, 0.65 mole) was added to a suspension of adenine (202.5 mg, 1.34 mmoles) in anhydrous DMF (10 ml). After stirring the mixture at room temperature for one hour, (3S,4S)-3,4-bis(benzoyloxymethyl)-7-oxabicyclo-[4.1.0]heptane (245 mg, 0.67 mmole) was added and the resulting mixture was heated in an oil bath kept at 140° C. for 3 hours. After adding 0.2M phosphate buffer (pH 7.0) to the reaction mixture and stirring the mixture for a while, the mixture was subjected to extraction with ethyl acetate. After drying the extract solution on anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride:methanol=50:1, v/v) to obtain 9-[(1R,2R,4S,5S)-4,5-bis(benzoyloxymethyl)-2-hydroxycyclohexyl]-adenine (161 mg, Yield 48%).

Workup

  1. temperaturethe resulting mixture was heated in an oil bath
  2. waitkept at 140° C. for 3 hours
  3. stirringstirring the mixture for a while
  4. extractionthe mixture was subjected to extraction with ethyl acetate
  5. dry with materialAfter drying the extract solution on anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride

Sources & evidence

ORD record
ord-73336e9fc4404977b11249c3cd543c26
Source dataset
uspto-grants-1994_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05374625

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes