Hydrochloric Acid → HCID 10660159, compound

HRID 1492474Notes

Reaction equation

HRID 1492474 reaction equation
C[O-].[Na+].C([O:12][CH2:13][C@@H:14]1[C@@H:19]([CH2:20][O:21]C(=O)C2C=CC=CC=2)[CH2:18][CH2:17][C@H:16]([N:30]2[CH:38]=[N:37][C:36]3[C:31]2=[N:32][CH:33]=[N:34][C:35]=3[NH2:39])[CH2:15]1)(=O)C1C=CC=CC=1.Cl>CO>[OH:12][CH2:13][C@@H:14]1[C@@H:19]([CH2:20][OH:21])[CH2:18][CH2:17][C@H:16]([N:30]2[CH:38]=[N:37][C:36]3[C:31]2=[N:32][CH:33]=[N:34][C:35]=3[NH2:39])[CH2:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 67823066HCID 67823066, compound

Product 1

HCID 10660159HCID 10660159, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (2.7 mg, 0.55 mole) was added to a solution of 9-[(1S,3S,4S)-3,4-bis(benzoyloxymethyl)cyclohexyl]-adenine (25 mg, 0.05 mole) in anhydrous methanol (2 ml) under cooling with ice. After stirring the mixture at room temperature overnight, the reaction mixture was neutralized with dilute hydrochloric acid and the solvent was distilled off under reduced pressure. Then, ethyl ether and water were added to the residue, the ethyl ether layer was removed, and the water was distilled off. Then, the residue was purified by Diaion HP-20 column chromatography (methanol concentration gradient) to obtain 9-[(1S,3S,4S)-3,4-bis(hydroxymethyl)-cyclohexyl]-adenine (9.4 mg, Yield 66.2%).

Workup

  1. temperatureunder cooling with ice
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThen, ethyl ether and water were added to the residue
  4. customthe ethyl ether layer was removed
  5. distillationthe water was distilled off
  6. customThen, the residue was purified by Diaion HP-20 column chromatography (methanol concentration gradient)

Sources & evidence

ORD record
ord-4c315d6804b44aeca440e75e8644a748
Source dataset
uspto-grants-1994_12
Patent number
US05374625

Reaction notes

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