HCID 18657707, compound → HCID 10199152, compound

HRID 1492465Notes

Reaction equation

HRID 1492465 reaction equation
Cl.O1CCOCC1.[Si]([O:25][CH2:26][C@@H:27]1[C@@H:31]([CH2:32][O:33][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:30][CH2:29][C@H:28]1[N:51]1[CH:59]=[N:58][C:57]2[C:52]1=[N:53][CH:54]=[N:55][C:56]=2[NH2:60])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>CO>[OH:25][CH2:26][C@@H:27]1[C@@H:31]([CH2:32][OH:33])[CH2:30][CH2:29][C@H:28]1[N:51]1[CH:59]=[N:58][C:57]2[C:52]1=[N:53][CH:54]=[N:55][C:56]=2[NH2:60]

Participants

4

Reactant 2

HCID 18657707HCID 18657707, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 10199152HCID 10199152, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4N-Hydrochloric acid/dioxane (0.17 ml, 0.68 mmole) was added to a solution of 9-[(1R,2R,3S)-2,3-bis-(t-butyldiphenylsilyloxymethyl)-1-cyclopentyl]-adenine (129 mg, 0.17 mmole) in methanol (1 ml). After stirring the mixture at room temperature overnight, solvent was distilled off from the reaction mixture under reduced pressure, after which water was added to the residue, ether-soluble material was removed therefrom, the residual solution was neutralized with 0.1N solution of sodium hydroxide, and solvent was distilled off therefrom. The residue was purified by Diaion HP-20 column chromatography (methanol concentration gradient) to obtain 9-[(1R,2R,3S)-2,3-bis(hydroxymethyl)-1-cyclopentyl]-adenine (43 mg, Yield 94%).

Workup

  1. distillationwas distilled off from the reaction mixture under reduced pressure
  2. additionafter which water was added to the residue, ether-soluble material
  3. customwas removed
  4. distillationwas distilled off
  5. customThe residue was purified by Diaion HP-20 column chromatography (methanol concentration gradient)

Sources & evidence

ORD record
ord-c8b7caff38494a3fb6a603b8fb297392
Source dataset
uspto-grants-1994_12
Patent number
US05374625

Reaction notes

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