Acetonitrile → HCID 86748330, compound

HRID 1492473Notes

Reaction equation

HRID 1492473 reaction equation
[C:1]([O:9][CH2:10][C@@H:11]1[C@@H:16]([CH2:17][O:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][C@@H:14]([N:27]2[CH:35]=[N:34][C:33]3[C:28]2=[N:29][CH:30]=[N:31][C:32]=3[NH2:36])[C@H:13]([OH:37])[CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(#N)C.[C:41]1([O:47][C:48](Cl)=[S:49])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CO>[C:1]([O:9][CH2:10][C@@H:11]1[C@@H:16]([CH2:17][O:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][C@@H:14]([N:27]2[CH:35]=[N:34][C:33]3[C:28]2=[N:29][CH:30]=[N:31][C:32]=3[NH2:36])[C@H:13]([O:37][C:48]([O:47][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[S:49])[CH2:12]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 70498Phenyl thioxochloroformateHCID 516892Sodium BicarbonateHCID 67823190HCID 67823190, compound

Product 1

HCID 86748330HCID 86748330, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Procedure

In an atmosphere of argon gas, 9-[(1R,2R,4S,5S)-4,5-bis(benzoyloxymethyl)-2-hydroxycyclohexyl]-adenine (151 mg, 0.3 mmole) was dissolved into acetonitrile (5 ml), to which were then added 4-dimethylaminopyridine (75.1 mg, 0.62 mmole) and phenyloxythiocarbonyl chloride (57 μl, 0.33 mmole). After stirring the resulting mixture at room temperature for 24 hours. 0.1M aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The extract solution was washed with water and then with saturated aqueous solution of sodium chloride and dried on anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 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-(phenoxythiocarbonyloxy)cyclohexyl]-adenine (109 mg, Yield 56.8%).

Workup

  1. extractionthe mixture was subjected to extraction with ethyl acetate
  2. washThe extract solution was washed with water
  3. dry with materialwith saturated aqueous solution of sodium chloride and dried on anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methylene chloride

Sources & evidence

ORD record
ord-b72c72d72e98420cb691a7b7a0f5fc41
Source dataset
uspto-grants-1994_12
Patent number
US05374625

Reaction notes

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