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

HRID 1846835노트

반응식

HRID 1846835 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fbead21a21044873b5cd46d8b433aabc
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952039B2

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