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

HRID 420837

반응식

HRID 420837 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 666573252',3'-di-O-methoxycarbonyl-5'-deoxy-5-fluoro-N4-(pentyloxycarbonyl) cytidine수율 91.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-2.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1cbe1ce39d054b469a44e82153c6c608
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097706B2

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