Hydrochloric Acid → 2',3'-di-O-methoxycarbonyl-5'-deoxy-5-fluoro-N4-(pentyloxycarbonyl) cytidine

HRID 420837

Reaktionsgleichung

Reaktionsgleichung von HRID 420837
[CH3:1][O:2][C:3]([O:5][C@@H:6]1[C@H:10]([O:11][C:12]([O:14][CH3:15])=[O:13])[C@@H:9]([CH3:16])[O:8][C@H:7]1[N:17]1[CH:24]=[C:23]([F:25])[C:21]([NH2:22])=[N:20][C:18]1=[O:19])=[O:4].N1C=CC=CC=1.Cl[C:33]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:34].Cl>ClCCl>[CH3:1][O:2][C:3]([O:5][C@@H:6]1[C@H:10]([O:11][C:12]([O:14][CH3:15])=[O:13])[C@@H:9]([CH3:16])[O:8][C@H:7]1[N:17]1[CH:24]=[C:23]([F:25])[C:21]([NH:22][C:33]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:34])=[N:20][C:18]1=[O:19])=[O:4]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 69489Pentyl chloroformateHCID 666574402',3'-di-O-methoxycarbonyl-5'-deoxy-5-fluorocytidine

Produkt 1

HCID 666573252',3'-di-O-methoxycarbonyl-5'-deoxy-5-fluoro-N4-(pentyloxycarbonyl) cytidineAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-2.5 °C

Versuchsvorschrift

35.8 g (0.099 mole) of the compound obtained in Example 2 was mixed with 163 ml of dichloromethane and 11 ml (0.136 mole) of pyridine, and stirred. After cooling the resulting mixture to −5 to 0° C., 15.7 ml (0.109 mole) of n-pentyl chloroformate was added dropwise thereto while maintaining the temperature of the reaction mixture at less than 0° C., followed adding the resulting mixture was warmed to room temperature and stirred for 2 hrs, 1 N HCl thereto. The organic layer was separated, successively washed with 163 ml of saturated sodium bicarbonate and 163 ml of water, dried over anhydrous sodium sulfate, and concentrated under a reduced pressure, to obtain 42.9 g of the title compound.

Aufarbeitung

  1. temperaturewhile maintaining the temperature of the reaction mixture at less than 0° C.
  2. additionfollowed adding the resulting mixture
  3. temperaturewas warmed to room temperature
  4. stirringstirred for 2 hrs
  5. customThe organic layer was separated
  6. washsuccessively washed with 163 ml of saturated sodium bicarbonate and 163 ml of water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1cbe1ce39d054b469a44e82153c6c608
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097706B2

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