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N,O-bis(trimethylsilyl)acetamide → HCID 89975754, 화합물

HRID 1508624
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HRID 1508624 반응식
[NH:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.Br[CH:22]1[C@@H:26]([F:27])[C@H:25]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[C@@H:24]([CH2:37][O:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)[S:23]1>C(Cl)Cl>[NH2:6][C:5]1[CH:7]=[CH:8][N:1]([CH:22]2[C@@H:26]([F:27])[C@H:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[C@@H:24]([CH2:37][O:38][CH2:39][C:40]3[CH:41]=[CH:42][C:43]([Cl:46])=[CH:44][CH:45]=3)[S:23]2)[C:2](=[O:3])[N:4]=1
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참가 물질

5

반응물 3

HCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 89975764HCID 89975764, 화합물HCID 178418229Cytosine

생성물 1

HCID 89975754HCID 89975754, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
80 °C

실험 절차

To another reaction vessel, 0.12 g of cytosine and 0.53 mL of N,O-bis(trimethylsilyl)acetamide were added in a nitrogen atmosphere, and the obtained mixture was then stirred at 80° C. for 2 hours. After cooling in air, a methylene chloride solution containing (3S,4S,5R)-2-bromo-4-((4-chlorobenzyl)oxy)-5-(((4-chlorobenzyl)oxy)methyl)-3-fluorothiolane was added to the reaction mixture, and the obtained mixture was then stirred 60° C. for 2 hours. Thereafter, methylene chloride was added to the reaction mixture, and the thus obtained mixture was washed with a saturated sodium hydrogen carbonate aqueous solution, and was then dried over anhydrous sodium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 80/20), so as to obtain 0.18 g of (3S,4S,5R)-2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4-((4-chlorobenzyl)oxy)-5-(((4-chlorobenzyl)oxy)methyl)-3-fluorothiolane in the form of a light yellow solid.

후처리

  1. temperatureAfter cooling in air
  2. additionwas added to the reaction mixture
  3. stirringthe obtained mixture was then stirred 60° C. for 2 hours
  4. washthe thus obtained mixture was washed with a saturated sodium hydrogen carbonate aqueous solution
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. distillationAfter that, the solvent was distilled away under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 80/20)

출처 및 근거

ORD 기록
ord-5d85fa26b4ff4d1f9dd6e6f66a34abcf
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09221865B2

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