Methanol → 2-Thioadenosine

HRID 1729608

Reaktionsgleichung

Reaktionsgleichung von HRID 1729608
O.[C@@H:2]1([N:11]2[C:20]3[C:14](=[C:15]([N+:17]([O-])=[CH:18][N:19]=3)[NH2:16])[N:13]=[CH:12]2)[O:10][C@H:7]([CH2:8][OH:9])[C@@H:5]([OH:6])[C@H:3]1[OH:4].[OH-].[Na+].CO.C(=S)=[S:27]>>[CH:12]1[N:11]([C@@H:2]2[O:10][C@H:7]([CH2:8][OH:9])[C@@H:5]([OH:6])[C@H:3]2[OH:4])[C:20]2[C:14](=[C:15]([NH2:16])[NH:17][C:18]([N:19]=2)=[S:27])[N:13]=1

Komponenten

5

Edukt 4

HCID 887MethanolHCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 178507182HCID 178507182, Verbindung

Produkt 1

HCID 64519652-ThioadenosineAusbeute 97 %

Versuchsvorschrift

8.0 g of adenosine 1-oxide monohydrate (26.67 mmol) was refluxed in 5 ml of a 5N sodium hydroxide aqueous solution for 15 minutes. The resulting liquid was neutralized to a pH of 9.0 using Amberlite IRC-50 (H+-type) and then concentrated to a small volume to prepare 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide oxime. To this was added 200 ml of an aqueous solution containing 175 ml of methanol. The pH of the resulting solution was 9. 50 ml of carbon disulfide was further added to the solution, and the mixture was allowed to react in an autoclave at 120° C for 5 hours under autogenous pressure (about 10 Kg/cm2). The orange colored substance formed in the autoclave was removed and concentrated to dryness. The residue was dissolved in 63 ml of 2.5N aqueous ammonia, and any impurities were filtered out. A mixture of n-butanol and acetic acid (125 ml:63 ml) was added to the above filtrate to crystallize the product to obtain 8.20 g of 2-thioadenosine having a melting point of 199° C (with decomposition) in a 97% yield.

Aufarbeitung

  1. concentrationconcentrated to a small volume
  2. customto prepare 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide oxime
  3. customto react in an autoclave at 120° C for 5 hours under autogenous pressure (about 10 Kg/cm2)
  4. customThe orange colored substance formed in the autoclave
  5. customwas removed
  6. concentrationconcentrated to dryness
  7. dissolutionThe residue was dissolved in 63 ml of 2.5N aqueous ammonia
  8. filtrationany impurities were filtered out
  9. additionA mixture of n-butanol and acetic acid (125 ml:63 ml)
  10. additionwas added to the above filtrate
  11. customto crystallize the product

Quellen und Nachweise

ORD-Eintrag
ord-b3a4c919e3dc4f889739101643e5dc92
Quelldatensatz
uspto-grants-1976_11
Patentnummer
US03989682

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