Hydrochloric Acid → HCID 135407359, compound

HRID 1492477Notes

Reaction equation

HRID 1492477 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:16][CH2:15][C@H:14]([CH2:17][O:18]C(=O)C3C=CC=CC=3)[C@@H:13]([CH2:27][O:28]C(=O)C3C=CC=CC=3)[CH2:12]2)=[C:4]([O:37]CCOC)[N:3]=1.C[O-].[Na+].Cl>CO>[OH:28][CH2:27][C@@H:13]1[C@@H:14]([CH2:17][OH:18])[CH2:15][CH2:16][C@H:11]([N:8]2[CH:7]=[N:6][C:5]3[C:4](=[O:37])[NH:3][C:2]([NH2:1])=[N:10][C:9]2=3)[CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 67822767HCID 67822767, compound

Product 1

HCID 135407359HCID 135407359, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Anhydrous methanol (1 ml) was added to 2-amino-9-[(1S,3S,4S)-3,4-bis(benzoyloxymethyl)-cyclohexyl]-6-(2-methoxyethoxy)-purine (17.4 mg, 0.03 mmole). While cooling the mixture with ice, sodium methoxide (1.62 mg, 0.03 mmole) was added thereto, and the whole mixture was stirred 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 mixture, an ethyl ether layer was removed, and water was distilled off. The residue was heated at 100° C. for one hour together with 2N aqueous hydrochloric acid (1 ml). After neutralizing the reaction mixture with 1N solution of sodium hydroxide, the reaction mixture was subjected to Diaion HP-20 column chromatography (methanol concentration gradient) to obtain 9-[(1S,3S,4S)-3,4-bis(hydroxymethyl)cyclohexyl]-guanine (5.7 mg, 31.3%).

Workup

  1. additionwas added
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThen, ethyl ether and water were added to the mixture
  4. customan ethyl ether layer was removed
  5. distillationwater was distilled off
  6. temperatureThe residue was heated at 100° C. for one hour together with 2N aqueous hydrochloric acid (1 ml)
  7. concentrationthe reaction mixture was subjected to Diaion HP-20 column chromatography (methanol concentration gradient)

Sources & evidence

ORD record
ord-0dcab03bc96b4922a3f0579464878097
Source dataset
uspto-grants-1994_12
Patent number
US05374625

Reaction notes

Loading…