Hydrochloric Acid → HCID 136401228, compound

HRID 1492476Notes

Reaction equation

HRID 1492476 reaction equation
C[O-].[Na+].[NH2:4][C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[C@@H:14]2[CH2:19][C@H:18]([CH2:20][O:21]C(=O)C3C=CC=CC=3)[C@@H:17]([CH2:30][O:31]C(=O)C3C=CC=CC=3)[CH2:16][C@H:15]2[OH:40])=[C:7]([O:41]CCOC)[N:6]=1.Cl>CO>[OH:31][CH2:30][C@@H:17]1[C@@H:18]([CH2:20][OH:21])[CH2:19][C@@H:14]([N:11]2[CH:10]=[N:9][C:8]3[C:7](=[O:41])[NH:6][C:5]([NH2:4])=[N:13][C:12]2=3)[C@H:15]([OH:40])[CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 67822896HCID 67822896, compound

Product 1

HCID 136401228HCID 136401228, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (36 mg, 0.67 mmole) was added to a solution of 2-amino-9-[(1R,2R,4S,5S)-4,5-bis(benzoyloxymethyl)-2-hydroxycyclohexyl]-6-(2-methoxyethoxy)-purine (190 mg, 0.33 mmole) in anhydrous methanol (3 ml) under cooling with ice. After stirring the mixture at room temperature for 5 hours, 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 water was distilled off. Then, the residue was heated at 100° C. for one hour together with 2N aqueous hydrochloric acid (7 ml). The reaction mixture was neutralized with 1N solution of sodium hydroxide and then purified by Diaion HP-20 column chromatography (methanol concentration gradient) to obtain 9-[(1R,2R,4S,5S)-4,5-bis(hydroxymethyl)-2-hydroxycyclohexyl]-guanine (70 mg, Yield 69%).

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. distillationwater was distilled off
  6. temperatureThen, the residue was heated at 100° C. for one hour together with 2N aqueous hydrochloric acid (7 ml)
  7. custompurified by Diaion HP-20 column chromatography (methanol concentration gradient)

Sources & evidence

ORD record
ord-eaa2331964b54d6785182decbbc6b987
Source dataset
uspto-grants-1994_12
Patent number
US05374625

Reaction notes

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