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5-Fluorouracil → [(2S,3S,4S,5S)-3,4-dibenzoyloxy-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate

HRID 744162
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HRID 744162 반응식
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.C(O[C@H:14]1[O:36][C@@H:35]([CH2:37][O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@H:25]([O:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:15]1[O:16][C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)C.C[Si](N[Si](C)(C)C)(C)C.Cl[Si](C)(C)C.Cl[Sn](Cl)(Cl)Cl>CC#N>[C:17]([O:16][C@H:15]1[C@@H:25]([O:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:35]([CH2:37][O:38][C:39](=[O:46])[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[O:36][C@@H:14]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 33855-FluorouracilHCID 6397ChlorotrimethylsilaneHCID 13838HexamethyldisilazaneHCID 24287Tin tetrachlorideHCID 10973190Ribofuranose, 1-acetate 2,3,5-tribenzoate

생성물 1

HCID 13827065[(2S,3S,4S,5S)-3,4-dibenzoyloxy-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
수율 61.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a mixture of 5-fluorouracil (0.85 g, 6.54 mmol) and compound 2 (3.0 g, 5.94 mmol) in anhydrous MeCN (100 ml) were successively added HMDS (1.25 ml, 5.95 mmol), ClSiMe3 (0.6 ml, 4.76 mmol) and SnCl4 (0.83 ml, 7.13 mmol). The resulting clear solution was refluxed for 1 hour when TLC indicated completion of the reaction. The solvent was evaporated and the residue dissolved in EtOAc (250 ml), washed with NaHCO3 and H2O. The EtOAc layer was dried, filtered and evaporated to give a white solid and it was crystallized from CHCl3 /MeOH (1-2%) to give compound 5 (2.11 g, 61.9%) as white crystals: m.p. 208°-209° C.

후처리

  1. temperatureThe resulting clear solution was refluxed for 1 hour when TLC
  2. customcompletion of the reaction
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in EtOAc (250 ml)
  5. washwashed with NaHCO3 and H2O
  6. dry with materialThe EtOAc layer was dried
  7. filtrationfiltered
  8. customevaporated
  9. customto give a white solid and it
  10. customwas crystallized from CHCl3 /MeOH (1-2%)

출처 및 근거

ORD 기록
ord-53dcae0d336b4abab98031f746b383bc
출처 데이터셋
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05559101

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