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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
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HRID 487648 반응식
[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]
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c173722bf2c847be835dff8ca6a8fbe3
출처 데이터셋
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05296492

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