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Phosphate → 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1-hydroxy-3-t-butyldimethylsilyloxypropyl)-1-pyridinyl}-2H-benzo[b]pyran

HRID 487648
ノート
印刷プレビュー

反応式

HRID 487648 の反応式
[C:1]([C:3]1[CH:26]=[CH:25][C:6]2[O:7][C:8]([CH3:24])([CH3:23])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH:17]([OH:21])[CH2:18][CH2:19][OH:20])=[CH:13][C:12]3=[O:22])[C:5]=2[CH:4]=1)#[N:2].C(N(CC)CC)C.[Si:34](Cl)([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35].P([O-])([O-])([O-])=O>C(Cl)Cl>[C:1]([C:3]1[CH:26]=[CH:25][C:6]2[O:7][C:8]([CH3:23])([CH3:24])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH:17]([OH:21])[CH2:18][CH2:19][O:20][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])=[CH:13][C:12]3=[O:22])[C:5]=2[CH:4]=1)#[N:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1061PhosphateHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 190925486-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1,3-dihydroxypropyl)-1-pyridinyl}-2H-benzo[b]pyran

生成物 1

HCID 217469036-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1-hydroxy-3-t-butyldimethylsilyloxypropyl)-1-pyridinyl}-2H-benzo[b]pyran収率 104%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

In 15 ml of anhydrous methylene chloride, is dissolved 1.06 g of 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1,3-dihydroxypropyl)-1-pyridinyl}-2H-benzo[b]pyran obtained in Example 37. Thereto are added 0.46 ml of triethylamine and 6 ml of a solution containing 0.48 g t-butyldimethylsilyl chloride in anhydrous methylene chloride at 0° C., and the resulting mixture is reacted at room temperature for 8 hours. After stopping the reaction by adding 0.2M phosphate buffer, the reaction mixture is extracted with methylene chloride. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The inorganic matter is filtered off and the filtrate is concentrated under reduced pressure. Thus, 1.46 g of 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1-hydroxy-3-t-butyldimethylsilyloxypropyl)-1-pyridinyl}-2H-benzo[b]pyran is obtained.

後処理

  1. customthe resulting mixture is reacted at room temperature for 8 hours
  2. customthe reaction
  3. extractionthe reaction mixture is extracted with methylene chloride
  4. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe inorganic matter is filtered off
  7. concentrationthe filtrate is concentrated under reduced pressure

出典と根拠

ORDレコード
ord-c173722bf2c847be835dff8ca6a8fbe3
出典データセット
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05296492

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート