Ethyl Acetate → 1-[(Diethylphosphonomethoxy)methoxymethyl]thymine

HRID 1551

반응식

HRID 1551 반응식
[C:1]([O:9][CH2:10][O:11][CH2:12][N:13]1[CH:21]=[C:19]([CH3:20])[C:17](=[O:18])[NH:16][C:14]1=[O:15])(=O)C1C=CC=CC=1.C([CH:24]([CH2:30]C)[O:25][P:26]([OH:29])([OH:28])=O)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[C:44](OCC)(=O)[CH3:45]>C1C=CC=CC=1>[CH2:44]([O:29][P:26]([CH2:1][O:9][CH2:10][O:11][CH2:12][N:13]1[CH:21]=[C:19]([CH3:20])[C:17](=[O:18])[NH:16][C:14]1=[O:15])([O:25][CH2:24][CH3:30])=[O:28])[CH3:45]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 65367Trimethylsilyl triflateHCID 148435351-[(Benzoyloxy)methoxymethyl]thymineHCID 54112757Pentan-3-yl dihydrogen phosphate

생성물 1

HCID 148865321-[(Diethylphosphonomethoxy)methoxymethyl]thymine

시약·촉매·용매 1

HCID 241Benzene용매

반응 조건

온도
85 °C

실험 절차

To a solution of 1-[(benzoyloxy)methoxymethyl]thymine (2.9 g, 10 mmol) and diethyl phosphonomethanol (1.85 g, 11 mmol) in benzene (180 mL) was added trimethylsilyl trifluoromethanesulfonate (0.05 mL) via a syringe under nitrogen. The solution was heated at 85° C. for 20 min. After cooling to room temperature, ethyl acetate (50 mL) was added and washed with aqueous bicarbonate, brine dried (MgSO4), filtered and concentrated in vacuo. The resultant yellow oil was purified by silica gel column chromatography using CH2Cl2 /5% MeOH as an eluent to give the title compound as a white oil: yield 980 mg (30%).

후처리

  1. temperatureAfter cooling to room temperature
  2. washwashed with aqueous bicarbonate, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resultant yellow oil was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-32e98db4036848ce8b8264c0ec0c3131
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726174

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