Trisodium Phosphate → Isotorabine

HRID 19491

Reaktionsgleichung

Reaktionsgleichung von HRID 19491
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][O:26]C(=O)C)[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]3[O:14][C:15](=[O:17])[CH3:16])[C:6]=2[N:7]=1.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>CC(C)=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][OH:26])[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]3[O:14][C:15](=[O:17])[CH3:16])[C:6]=2[N:7]=1

Komponenten

4

Edukt 2

HCID 24243Trisodium PhosphateHCID 116332675-Amino-3-(2',3,5'-tri-O-acetyl-beta-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one

Produkt 1

HCID 11234476Isotorabine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a clear solution of 78 (500 mg) in acetone (5 mL) was added sodium phosphate buffer (pH=7.0, 0.1 M, 25 mL), upon which the solution became cloudy (white precipitate). Candida antarctica lipase resin (250 mg) was added to the mixture and the suspension was subsequently gently shaken for 10 h at room temperature. The resulting clear mixture was filtered, and organic solvent was removed under vacuum. The aqueous solution was then extracted with ethyl acetate (3×25 mL) and the organic layers were combined, dried over MgSO4, and concentrated. The resulting solid could be further purified in a manner similar to that described in Example 43, step 3.

Aufarbeitung

  1. filtrationThe resulting clear mixture was filtered
  2. customorganic solvent was removed under vacuum
  3. extractionThe aqueous solution was then extracted with ethyl acetate (3×25 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting solid could be further purified in a manner similar to

Quellen und Nachweise

ORD-Eintrag
ord-8553f3f407f5462680d176d3a9b20f55
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745415B2

Verknüpfte Notizen

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