Sodium hydride → 3'-O-(4-chloro-2-fluorobenzyl)-2'-deoxy-5-fluorouridine

HRID 362184

Reaktionsgleichung

Reaktionsgleichung von HRID 362184
C([O:20][CH2:21][C@H:22]1[O:26][C@@H:25]([N:27]2[CH:34]=[C:33]([F:35])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24][C@@H:23]1[OH:36])(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[H-].[Na+].[Cl:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44]Br)=[C:42]([F:48])[CH:41]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44][O:36][C@@H:23]2[C@@H:22]([CH2:21][OH:20])[O:26][C@@H:25]([N:27]3[CH:34]=[C:33]([F:35])[C:31](=[O:32])[NH:30][C:28]3=[O:29])[CH2:24]2)=[C:42]([F:48])[CH:41]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27365514-Chloro-2-fluorobenzyl bromideHCID 108387042'-deoxy-5'-O-trityl-5-fluorouridine

Produkt 1

HCID 229422143'-O-(4-chloro-2-fluorobenzyl)-2'-deoxy-5-fluorouridineAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The title compound was prepared according to the process disclosed in Japanese Unexamined Patent Publication No. 106593/1986. The process was carried out as follows. A 5.0 g quantity of 2'-deoxy-5'-O-trityl-5-fluorouridine was dissolved in 40 ml of tetrahydrofuran. To the solution was added 856 mg of 60% sodium hydride, followed by 1 hour of stirring at room temperature. After addition of 2.58 g of 4-chloro-2-fluorobenzyl bromide, the mixture was stirred at room temperature for 2 hours. The reaction mixture was cooled to 0° C. and saturated ammonium chloride was added in excess. The tetrahydrofuran layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off at reduced pressure, and the residue was purified by silica gel column chromatography (eluate: n-hexane-ethyl acetate (3:2)), giving 5.03 g of the title compound (yield 78%).

Aufarbeitung

  1. customThe title compound was prepared
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. washThe tetrahydrofuran layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off at reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluate: n-hexane-ethyl acetate (3:2))

Quellen und Nachweise

ORD-Eintrag
ord-7bb94f65b9994d268c00eb7c72689858
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869464

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