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

HRID 1694887Notes

Reaction equation

HRID 1694887 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]([CH:32]([CH3:34])[CH3:33])[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]([CH:32]([CH3:34])[CH3:33])[C:29](=[O:31])[O:30]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 66645582(3S,5S)-5-[(S)-1-amino-2-hydroxyethyl]-3-isopropyldihydrofuran-2-one hydrochloride

Product 1

HCID 54578740N-{(S)-2-hydroxy-1-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamideYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

14 ml of triethylamine (101 mmol) and 11.12 g of O-nitrobenzenesulfonyl chloride (50.1 mmol) were added to a solution of 8.50 g of (3S,5S)-5-[(S)-1-amino-2-hydroxyethyl]-3-isopropyldihydrofuran-2-one hydrochloride obtained in the above reaction (33.5 mmol) in a mixed solvent of tetrahydrofuran (170 ml) and water (17 ml) at room temperature, and the mixture was stirred at the same temperature for 12 hours. The reaction mixture was concentrated under reduced pressure, 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, 110 ml of diisopropyl ether and 11 ml of ethyl acetate were added, and the precipitated solid was collected by filtration to obtain 8.78 g of the title compound (total yield over two steps: 70%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionfollowed by extraction with ethyl acetate
  3. washThen, the organic layer was washed with water
  4. dry with materiala saturated sodium bicarbonate aqueous solution and brine and dried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent:ethyl acetate)
  8. additionFurther, 110 ml of diisopropyl ether and 11 ml of ethyl acetate were added
  9. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-1a8e5ba37d6147f38eae68004788f2f7
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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