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

HRID 1847064Notes

Reaction equation

HRID 1847064 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 867249904-[(3S)-3,4-dihydroxybutyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

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 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)

Sources & evidence

ORD record
ord-7d94bff4c7364a8dbfc850b0aae400ab
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

Loading…