4-Toluenesulfonyl chloride → (2R)-2-Hydroxy-4-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)butyl 4-methylbenzensulfonate

HRID 1847071Notes

Reaction equation

HRID 1847071 reaction equation
[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

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 867249944-[(3R)-3,4-Dihydroxybutyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

Product 1

HCID 86724995(2R)-2-Hydroxy-4-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)butyl 4-methylbenzensulfonateYield 62.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (80 ml) was dissolved 4-[(3R)-3,4-dihydroxybutyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (4.38 g, 16.51 mmol) and triethylamine (2.76 ml, 19.81 mmol), dimethylamino pyridine (403 mg, 3.30 mmol) and p-toluene sulfonyl chloride (3.46 g, 18.16 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 over 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 4.30 g (62%) of the title compound in the form of an orange oily product.

Workup

  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 over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-9863a59283bc402387830863a520a22d
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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