4-Methoxybenzenesulfonyl chloride → N-[4-methoxybenzenesulfonyl]-(D)-asparagine

HRID 742058

反応式

HRID 742058 の反応式
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].C(N(CC)CC)C.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>O1CCOCC1.O>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([NH:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])(=[O:27])=[O:26])=[CH:23][CH:24]=1

参加物

6

反応物 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 439600D-Asparagine

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
0 °C

実験手順

D-asparagine (13.2 g, 100.0 mmol) is dissolved in dioxane (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.

後処理

  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

出典と根拠

ORDレコード
ord-1994d66083674cf799c8b45050933a17
出典データセット
uspto-grants-1996_09
特許番号
US05552419

関連ノート

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