2',3',5'-tri-O-acetyladenosine → N6-(3,3-diphenylthio-5-oxo-2-pyrrolidinyl)adenosine 2',3',5'-triacetate

HRID 358010Notes

Reaction equation

HRID 358010 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[C:28]2[N:27]=[CH:26][N:25]=[C:23]([NH2:24])[C:22]=2[N:21]=[CH:20]1)(=[O:3])[CH3:2].[C:29]1([S:35][C:36]2([S:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH2:40][CH:39]([O:41]CC)[NH:38][C:37]2=O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1(C)C=CC=CC=1>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[C:28]2[N:27]=[CH:26][N:25]=[C:23]([NH:24][CH:37]3[C:36]([S:35][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)([S:45][C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)[CH2:40][C:39](=[O:41])[NH:38]3)[C:22]=2[N:21]=[CH:20]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 965032',3',5'-tri-O-acetyladenosineHCID 131459153,3-Diphenylthio-5-ethoxy-2-pyrrolidinone

Product 1

HCID 131713627N6-(3,3-diphenylthio-5-oxo-2-pyrrolidinyl)adenosine 2',3',5'-triacetateYield 55.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Adenosine 2',3',5'-triacetate (110 mg) and 3,3-diphenylthio-5-ethoxy-2-pyrrolidinone (155 mg) were heated in toluene (10 ml) under reflux for 5 hours, at the end of which the reaction solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography using chloroform-acetone (5:1) as the eluent. The active fractions were pooled and concentrated under reduced pressure to give crystals which were recrystallized from ethanol. By the above procedure was obtained N6 -(3,3-diphenylthio-5-oxo-2-pyrrolidinyl)adenosine 2',3',5'-triacetate as colorless needles (108 mg).

Workup

  1. temperatureunder reflux for 5 hours, at the end of which the reaction solvent
  2. distillationwas distilled off under reduced pressure
  3. concentrationconcentrated under reduced pressure
  4. customto give crystals which
  5. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-21944e8626df403899b679d5441f4bfe
Source dataset
uspto-grants-1984_08
Patent number
US04464361

Reaction notes

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