Tetrahydrofuran → N-{(S)-2-hydroxy-1-[(2S,4R)-5-oxo-4-propyltetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide

HRID 1695011Notes

Reaction equation

HRID 1695011 reaction equation
C(N(CC)CC)C.[CH:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([S:17](Cl)(=[O:19])=[O:18])=[CH:10][CH:9]=1.Cl.[NH2:22][C@H:23]([C@H:26]1[O:30][C:29](=[O:31])[C@H:28]([CH2:32][CH2:33][CH3:34])[CH2:27]1)[CH2:24][OH:25].O1CCCC1>O>[OH:25][CH2:24][C@H:23]([NH:22][S:17]([C:11]1[CH:10]=[CH:9][CH:8]=[CH:13][C:12]=1[N+:14]([O-:16])=[O:15])(=[O:19])=[O:18])[C@@H:26]1[CH2:27][C@@H:28]([CH2:32][CH2:33][CH3:34])[C:29](=[O:31])[O:30]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 66645499(3R,5S)-5-[(S)-1-amino-2-hydroxyethyl]-3-propyldihydrofuran-2-one hydrochloride

Product 1

HCID 66645749N-{(S)-2-hydroxy-1-[(2S,4R)-5-oxo-4-propyltetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamideYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

23.9 g of triethylamine (237 mmol) and 26.7 g of O-nitrobenzenesulfonyl chloride (120 mmol) were added to a solution of (3R,5S)-5-[(S)-1-amino-2-hydroxyethyl]-3-propyldihydrofuran-2-one hydrochloride obtained in the above reaction in a mixed solvent of tetrahydrofuran (350 ml) and water (35.0 ml) at 0° C. The mixture was stirred at the same temperature for two hours and further stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure and 500 ml of water was added, followed by extraction with ethyl acetate. Then, the organic layer was washed with water, a saturated sodium bicarbonate aqueous solution and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:ethyl acetate). Further, 30 ml of diisopropyl ether and 30 ml of ethyl acetate were added, and the precipitated solid was collected by filtration to obtain 14.6 g of the title compound (total yield over two steps: 52%).

Workup

  1. stirringfurther stirred at room temperature for 12 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure and 500 ml of water
  3. additionwas added
  4. extractionfollowed by extraction with ethyl acetate
  5. washThen, the organic layer was washed with water
  6. dry with materiala saturated sodium bicarbonate aqueous solution and brine and dried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. customthe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (elution solvent:ethyl acetate)
  10. additionFurther, 30 ml of diisopropyl ether and 30 ml of ethyl acetate were added
  11. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-0554055088114bfc8345673c14e5c847
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

Loading…