Methanol → HCID 10643625, 화합물

HRID 2271254노트

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HRID 2271254 반응식
[CH2:1]([Si:3]([C:8]#[C:9][C@:10]1([CH2:32][O:33]CC2C=CC=CC=2)[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[C@H:12]([OH:23])[C@@H:11]1[O:24]CC1C=CC=CC=1)([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].B(Cl)(Cl)Cl.N1C=CC=CC=1.CO>ClCCl>[CH2:1]([Si:3]([C:8]#[C:9][C@:10]1([CH2:32][OH:33])[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[C@H:12]([OH:23])[C@@H:11]1[OH:24])([CH2:4][CH3:5])[CH2:6][CH3:7])[CH3:2]

참가 물질

6

반응물 4

HCID 887MethanolHCID 1049PyridineHCID 25135Boron TrichlorideHCID 107455044'-C-triethylsilylethynyl-3',5'-di-O-benzyluridine

생성물 1

HCID 10643625HCID 10643625, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Compound 8 (1.50 g, 2.67 mmol) was dissolved in dichloromethane (75.0 ml), and a 1.0 M boron trichloride (26.7 ml, 26.7 mmol) in dichloromethane was added to the solution at −78° C. in an argon atmosphere, followed by stirring for three hours at the same temperature. A mixture of pyridine (10.0 ml) and methanol (20.0 ml) was added thereto at −78° C., followed by stirring for ten minutes. The reaction mixture was concentrated through distillation under reduced pressure, and the residue was partitioned with ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate and concentrated through distillation under reduced pressure. The residue was purified by means of silica gel column chromatography (silica gel 200 ml, eluent; chloroform:methanol=9:1), to thereby yield a white powdery compound (Compound 9; 0.95 g, 2.48 mmol, 92.9%).

후처리

  1. additionwas added
  2. customat −78° C.
  3. stirringby stirring for ten minutes
  4. concentrationThe reaction mixture was concentrated through distillation under reduced pressure
  5. customthe residue was partitioned with ethyl acetate and water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated through distillation under reduced pressure
  8. customThe residue was purified by means of silica gel column chromatography (silica gel 200 ml, eluent; chloroform:methanol=9:1)

출처 및 근거

ORD 기록
ord-cacddde5f77d42cdab1f46098db3e78a
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06333315B1

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