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Chlorosuccinimide → 2,2-Dimethylpropionic acid [8-chloro-3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester

HRID 1792056
Notes
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Reaction equation

HRID 1792056 reaction equation
[CH3:1][C:2]([CH3:27])([CH3:26])[C:3]([O:5][CH2:6][N:7]1[C:15]2[N:14]=[CH:13][NH:12][C:11]=2[C:10](=[O:16])[N:9]([CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[C:8]1=[O:25])=[O:4].[Cl:28]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Cl:28][C:13]1[NH:12][C:11]2[C:10](=[O:16])[N:9]([CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:21])([CH3:23])[CH3:22])[C:8](=[O:25])[N:7]([CH2:6][O:5][C:3](=[O:4])[C:2]([CH3:27])([CH3:26])[CH3:1])[C:15]=2[N:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 153324012,2-Dimethylpropionic acid [3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester

Product 1

HCID 235368892,2-Dimethylpropionic acid [8-chloro-3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl esterYield 63.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

2,2-Dimethylpropionic acid [3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester (2.31 g) was dissolved in N,N-dimethylformamide (18 ml), and N-chlorosuccinimide (973 mg) was added to the solution while cooling on ice. Then, the mixture was stirred for 10 minutes on ice, and then at room temperature for 20 hours. The obtained reaction mixture was diluted with ethyl acetate, washed with water, and dried over anhydrous magnesium sulfate. After removing the solvent by distillation from the organic layer, the residue was purified by silica gel column chromatography to give 1.61 g of the title compound from the elution fraction of hexane-ethyl acetate (1:1).

Workup

  1. temperaturewhile cooling on ice
  2. waitat room temperature for 20 hours
  3. customThe obtained reaction mixture
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removing the solvent
  7. distillationby distillation from the organic layer
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dd295e1eb51349869bd96a72eccdf9bd
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07074798B2

Reaction notes

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