Triethylamine → 3'-O-benzyl-2'-deoxy-3-(2-tetrahydrofuranyl)-5-fluorouridine

HRID 466092

반응식

HRID 466092 반응식
[CH2:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][OH:15])[O:12][C@@H:11]([N:16]2[CH:23]=[C:22]([F:24])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:29]1[CH2:33][CH2:32][CH2:31][O:30]1)(=O)C.C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][OH:15])[O:12][C@@H:11]([N:16]2[CH:23]=[C:22]([F:24])[C:20](=[O:21])[N:19]([CH:29]3[CH2:33][CH2:32][CH2:31][O:30]3)[C:17]2=[O:18])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 102657Tetrahydro-2-furyl acetateHCID 10664574Uridine, 2'-deoxy-5-fluoro-3'-O-(phenylmethyl)-

생성물 1

HCID 137150913'-O-benzyl-2'-deoxy-3-(2-tetrahydrofuranyl)-5-fluorouridine수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A 1.32 g quantity of N,O-bis(trimethylsiliyl)-acetamide was added with stirring to a suspension of 0.40 g of 3'-O-benzyl-2'-deoxy-5-fluorouridine in 8 ml of dry dichloromethane at room temperature. To the mixture were added, after 4 hours, 0.32 g of 2-acetoxytetrahydrofuran and a solution of 0.1 ml of stannic chloride in 1.6 ml of dry dichloromethane. The mixture was stirred for 1.5 hours and neutralized with 0.64 ml of triethylamine and washed with water. The dichloromethane layer was concentrated and the residue was dissolved in 16 ml of methanol. To the solution was added 0.24 ml of acetic acid and the mixture was left to stand for 3 hours at 40° C. The solvent was distilled off and the residue was subjected to silica gel column chromatography to conduct a gradient elution using chloroform and mixtures of methanol (up to 4%) and chloroform, giving 0.3 g of the title compound in a yield of 77%.

후처리

  1. additionTo the mixture were added, after 4 hours
  2. washwashed with water
  3. concentrationThe dichloromethane layer was concentrated
  4. dissolutionthe residue was dissolved in 16 ml of methanol
  5. additionTo the solution was added 0.24 ml of acetic acid
  6. waitthe mixture was left
  7. waitto stand for 3 hours at 40° C
  8. distillationThe solvent was distilled off
  9. washa gradient elution

출처 및 근거

ORD 기록
ord-de69e7d23ed543889cc9bb5412f07d5b
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155113

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