Methanol → N-(5-benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide

HRID 1846835Notes

Reaction equation

HRID 1846835 reaction equation
[OH:1][C:2]1[C:3](=[O:21])[CH:4]=[C:5]([CH2:10][NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[O:6][C:7]=1[CH2:8][OH:9].CO.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([O:1][C:2]1[C:3](=[O:21])[CH:4]=[C:5]([CH2:10][NH:11][S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])[O:6][C:7]=1[CH2:8][OH:9])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 7498Benzyl BromideHCID 86725692N-(5-hydroxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide

Product 1

HCID 86725693N-(5-benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamideYield 46.5%

Procedure

To a stirred solution of N-(5-hydroxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide (9-01) (1.7 g, 5.46 mmol) in methanol (30 mL) aqueous NaOH (218.4 mg, 5.46 mmol, 2M) was added. After heating to reflux, benzyl bromide (0.654 mL, 5.46 mmol) was added and heating was continued for 24 h. After completion of the reaction, the mixture was concentrated to remove methanol, then diluted with water and extracted with dichloromethane. The combined organic layer was washed with saturated NaHCO3 solution, water and brine, dried over Na2SO4 and concentrated under reduced pressure. It was then purified using normal column chromatography to get N-(5-benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide (10-01) (1.02 gm, 46.48%) as a white solid.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux
  3. temperatureheating
  4. customAfter completion of the reaction
  5. concentrationthe mixture was concentrated
  6. customto remove methanol
  7. additiondiluted with water
  8. extractionextracted with dichloromethane
  9. washThe combined organic layer was washed with saturated NaHCO3 solution, water and brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated under reduced pressure
  12. customIt was then purified

Sources & evidence

ORD record
ord-fbead21a21044873b5cd46d8b433aabc
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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