Methanol → HCID 10643625、化合物

HRID 1597064ノート

反応式

HRID 1597064 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 10643625HCID 10643625、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-d9979527f1934108a6447ceb2c51c7b0
出典データセット
uspto-grants-2001_09
特許番号
US06291670B1

反応ノート

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