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4-Toluenesulfonyl chloride → (2S)-2-hydroxy-4-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)butyl 4-methylbenzenesulfonate

HRID 1847064
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HRID 1847064 반응식
[OH:1][C@H:2]([CH2:18][OH:19])[CH2:3][CH2:4][N:5]1[C:10](=[O:11])[CH:9]=[N:8][C:7]2[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[N:15][C:6]1=2.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:36]1([CH3:46])[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1>ClCCl.O>[CH3:46][C:36]1[CH:41]=[CH:40][C:39]([S:42]([O:19][CH2:18][C@@H:2]([OH:1])[CH2:3][CH2:4][N:5]2[C:10](=[O:11])[CH:9]=[N:8][C:7]3[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[N:15][C:6]2=3)(=[O:44])=[O:43])=[CH:38][CH:37]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 867249904-[(3S)-3,4-dihydroxybutyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

생성물 1

HCID 86724989(2S)-2-hydroxy-4-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)butyl 4-methylbenzenesulfonate수율 72%

시약·촉매·용매 2

HCID 962Water용매
HCID 6344Dichloromethane용매

실험 절차

In dichloromethane (4 ml) was dissolved 4-[(3S)-3,4-dihydroxybutyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (200 mg, 0.754 mmol), and triethylamine (0.126 ml, 0.905 mmol), dimethylamino pyridine (18.4 mg, 0.151 mmol) and p-toluene sulfonyl chloride (158 mg, 0.829 mmol) were added thereto under cooling on ice and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, water was added to the reaction solution which was extracted with dichloromethane. After drying the extract with anhydrous sodium sulfate, the solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (chloroform/methanol) to yield 227 mg (72%) of the title compound in the form of a yellow oily product.

후처리

  1. additionwere added
  2. temperatureunder cooling on ice
  3. additionwas added to the reaction solution which
  4. extractionwas extracted with dichloromethane
  5. customAfter drying the
  6. extractionextract with anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

출처 및 근거

ORD 기록
ord-7d94bff4c7364a8dbfc850b0aae400ab
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952010B2

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