Hydrochloric Acid → HCID 67822841, compound

HRID 1492472Notes

Reaction equation

HRID 1492472 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][C@@H:17]([N:30]2[CH:38]=[N:37][C:36]3[C:31]2=[N:32][CH:33]=[N:34][C:35]=3[NH2:39])[C@H:16]([OH:40])[CH2:15]1)(=O)C1C=CC=CC=1.CO.Cl>C1COCC1>[OH:12][CH2:13][C@@H:14]1[C@@H:19]([CH2:20][OH:21])[CH2:18][C@@H:17]([N:30]2[CH:38]=[N:37][C:36]3[C:31]2=[N:32][CH:33]=[N:34][C:35]=3[NH2:39])[C@H:16]([OH:40])[CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 67823190HCID 67823190, compound

Product 1

HCID 67822841HCID 67822841, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium methoxide (40 mg, 0.74 mmole) was added to a solution of 9-[(1R,2R,4S,5S)-4,5-bis(benzoyloxymethyl)-2-hydroxycyclohexyl]-adenine (185 mg, 0.37 mmole) in a solvent mixture consisting of anhydrous methanol (4 ml) and anhydrous THF (4 ml) under ice cooling. After stirring the resulting mixture at room temperature for 5 hours, the reaction mixture was neutralized with dilute hydrochloric acid, and the solvent was distilled off therefrom under reduced pressure. The residue was purified by Diaion HP-20 column chromatography (methanol concentration gradient) to obtain 9-[(1R,2R,4S,5S)-4,5-bis(hydroxymethyl)-2-hydroxycyclohexyl]-adenine (109 mg, Yield 100%).

Workup

  1. distillationthe solvent was distilled off
  2. customThe residue was purified by Diaion HP-20 column chromatography (methanol concentration gradient)

Sources & evidence

ORD record
ord-ba0b4ea386514a19a22ce2d774e99da2
Source dataset
uspto-grants-1994_12
Patent number
US05374625

Reaction notes

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