Acetic Acid → 9-((2S,3S,4R,5S)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one

HRID 744167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 744167
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[N:34]1[CH:42]=[N:41][C:40]2[C:35]1=[N:36][CH:37]=[N:38][C:39]=2Cl)(=O)C1C=CC=CC=1.SC([OH:47])C.C[O-].[Na+].C(O)(=O)C>CO>[C@H:11]1([N:34]2[CH:42]=[N:41][C:40]3[C:39](=[O:47])[NH:38][CH:37]=[N:36][C:35]2=3)[O:12][C@@H:13]([CH2:24][OH:25])[C@H:14]([OH:15])[C@@H:10]1[OH:9]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 4713212Mercapto-ethanolHCID 10942334Sodium MethoxideHCID 86749850[(2S,3S,4S,5S)-3,4-dibenzoyloxy-5-(6-chloropurin-9-yl)oxolan-2-yl]methyl benzoate

Produkt 1

HCID 1355222619-((2S,3S,4R,5S)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-oneAusbeute 1.359,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 9 (1.05 g, 1.70 mmol), mercaptoethanol (0.48 ml, 6.9 mmol), and NaOMe in MeOH (100 ml) was refluxed for four hours. The reaction mixture was cooled, neutralized with glacial acetic acid and evaporated to dryness. The solid obtained was washed with CHCl3 and the residue was crystallized from EtOH to give pure 11 (6.198 g, 47%) as white crystals: m.p. 212°-213° C. (dec).

Aufarbeitung

  1. temperaturewas refluxed for four hours
  2. temperatureThe reaction mixture was cooled
  3. customevaporated to dryness
  4. customThe solid obtained
  5. washwas washed with CHCl3
  6. customthe residue was crystallized from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-794e0b8755f44ed58195358b0017c76e
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05559101

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