5'-O-(4,4'-Dimethoxytrityl)thymidine → 3'-O-[2-(2-nitrophenyl)propoxycarbonyl]thymidine

HRID 354213

반응식

HRID 354213 반응식
COC1C=CC(C([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]3=[O:31])[CH2:26][C@@H:25]2[OH:38])(C2C=CC=CC=2)C2C=CC(OC)=CC=2)=CC=1.[Cl-].[N+:42]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[CH:51]([CH3:62])[CH2:52][O:53][C:54](N1C=C[N+](C)=C1)=[O:55])([O-:44])=[O:43]>ClCCl>[N+:42]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[CH:51]([CH3:62])[CH2:52][O:53][C:54]([O:38][C@@H:25]1[C@@H:24]([CH2:23][OH:22])[O:28][C@@H:27]([N:29]2[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]2=[O:31])[CH2:26]1)=[O:55])([O-:44])=[O:43]

참가 물질

4

반응물 2

HCID 1624195'-O-(4,4'-Dimethoxytrityl)thymidineHCID 11232610N3-[2-(2-nitrophenyl)propoxycarbonyl]-N-methyl imidazolium chloride

생성물 1

HCID 113398703'-O-[2-(2-nitrophenyl)propoxycarbonyl]thymidine수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

A solution of 2 g 5′-O-(4,4′-dimethoxytrityl)thymidine (3) (3.67 mmol) in 20 ml dichloromethane is added dropwise at 0° C. to 1.2 equiv N3-[2-(2-nitrophenyl)propoxycarbonyl]-N-methylimidazolium chloride (2) (4.4 mmol) in 30 ml dichloromethane through a molecular sieve 4 Å within 10 minutes. The reaction mixture was stirred at 0° C. overnight, then extracted using 0.5% HCl (100 ml), dried via Na2SO4 and evaporated. 10% trichloroacetic acid (70 ml) in dichloromethane is added to the organic phase and stirred for 2 minutes. Thereafter, the deep-red solution is extracted twice using saturated NaHCO3 (100 ml), dried via Na2SO4 and evaporated. Purification via flash chromatography (0-10% methanol in toluene/ethyl acetate (5:4)) yielded 1.53 g (93%) of the title compound.

후처리

  1. extractionextracted
  2. dry with materialdried via Na2SO4
  3. customevaporated
  4. addition10% trichloroacetic acid (70 ml) in dichloromethane is added to the organic phase
  5. stirringstirred for 2 minutes
  6. extractionThereafter, the deep-red solution is extracted twice using saturated NaHCO3 (100 ml)
  7. dry with materialdried via Na2SO4
  8. customevaporated
  9. customPurification via flash chromatography (0-10% methanol in toluene/ethyl acetate (5:4))

출처 및 근거

ORD 기록
ord-e48f496d38c3476a976914d31e1d406e
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756492B1

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