Water → N-[4-methoxybenzenesulfonyl]-(D)-asparagine

HRID 2209709

반응식

HRID 2209709 반응식
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].O.C(N(CC)CC)C.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>O1CCOCC1>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])(=[O:28])=[O:27])=[CH:24][CH:25]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 439600D-Asparagine

생성물 1

HCID 27014145N-[4-methoxybenzenesulfonyl]-(D)-asparagine

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
0 °C

실험 절차

D-asparagine (13.2 g, 100.0 mmol) is dissolved in dioxane 1,75.0 mL) and water (125.0 mL), triethylamine (21.0 mL, 150.0 mmol) is added, and the solution is cooled to 0° C. To this solution is added 4-methoxybenzenesulfonyl chloride (22.7 g, 110.0 mmol) over 10 minutes. The reaction is warmed to room temperature and stirred for 3 days. The precipitate is then filtered off, the filtrate is acidified to pH=~4, and extracted well with ethyl acetate. A first crop of pure product precipitates from the ethyl acetate and is collected by filtration. A second crop is obtained by evaporating off the ethyl acetate, and rinsing the solid obtained with water to remove inorganic salts. The two crops are combined to give N-[4-methoxybenzenesulfonyl]-(D)-asparagine.

후처리

  1. temperatureThe reaction is warmed to room temperature
  2. filtrationThe precipitate is then filtered off
  3. extractionextracted well with ethyl acetate
  4. customA first crop of pure product precipitates from the ethyl acetate
  5. filtrationis collected by filtration
  6. customA second crop is obtained
  7. customby evaporating off the ethyl acetate
  8. washrinsing the solid
  9. customobtained with water
  10. customto remove inorganic salts

출처 및 근거

ORD 기록
ord-186a678734c54e59bc312368c8900fe1
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05455258

연결된 노트

불러오는 중…