Acetic Anhydride → 1-(3-O-acetyl-2,5-dideoxy-5-iodo-beta-D-threopentofuranosyl)thymine

HRID 1181912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1181912
[I:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@H:4]1[OH:17].[C:18](OC(=O)C)(=[O:20])[CH3:19]>N1C=CC=CC=1>[C:18]([O:17][C@H:4]1[C@@H:3]([CH2:2][I:1])[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5]1)(=[O:20])[CH3:19]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 128500761-(2,5-dideoxy-5-iodo-beta-D-threo-pentofuranosyl)thymine

Produkt 1

HCID 121116121-(3-O-acetyl-2,5-dideoxy-5-iodo-beta-D-threopentofuranosyl)thymineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-(2,5-dideoxy-5-iodo-β-D-threo-pentofuranosyl)thymine (for preparation see ref. J. Org. Chem. 1964, 29, 2076) (5.1 g, 14.5 mmol) in anhydrous pyridine (50 mL) at 0° C. under argon was added acetic anhydride (7.0 ml, 75.4 mmol). The reaction mixture was stirred at room temperature for 17 h. The reaction mixture was cooled with ice bath and quenched by slow addition of water (15 mL). The reaction mixture was stirred for 30 min and concentrated to dryness, and co-evaporated with anhydrous toluene three times. The residue was re-dissolved in dichloromethane and chromatographed on silica gel with 1-3% methanol in ethyl acetate gave 4.4 g of 1-(3-O-acetyl-2,5-dideoxy-5-iodo-β-D-threo-pentofuranosyl)thymine (49).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled with ice bath
  2. customquenched by slow addition of water (15 mL)
  3. stirringThe reaction mixture was stirred for 30 min
  4. concentrationconcentrated to dryness
  5. dissolutionThe residue was re-dissolved in dichloromethane
  6. customchromatographed on silica gel with 1-3% methanol in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ab701c16beda478e803e1f513f351e98
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285658B2

Notizen zur Reaktion

Wird geladen…