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

HRID 1157347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1157347
[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-9b0e5c3b89ef4615bdcc0fa236278fef
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807653B2

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