(-)-Asparagine → N-Phenysulfonyl-L-asparagine

HRID 265882ノート

反応式

HRID 265882 の反応式
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[OH-].[Na+].O1CCOCC1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[C:18]1([S:24]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 6267(-)-AsparagineHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium Hydroxide2 回HCID 312751,4-Dioxane

生成物 1

HCID 10754635N-Phenysulfonyl-L-asparagine

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

To a stirred solution of L-asparagine (Aldrich) (10 g, 76 mmol), NaOH (3.4 g, 85 mmol), H2O (50 mL), and dioxane (50 mL) at 0° C. was added PhSO2Cl (10.6 mL, 84 mmol). After I min, NaOH (3.4 g) in H2O (50 mL) was added and the reaction mixture stirred for 30 min. The reaction mixture was then concentrated to remove the dioxane then washed with EtOAc. The aqueous phase was then cooled to 0° C. and acidified to pH with cone. HCl to effect product precipitation. The resulting solid was collected by filtration, washed with H2O (20 mL) and dried at 50° C. under vacuum to give 19-1 as a white solid. Rf 0.40 (silica, 10:1:1 ethanol/H2O/NH4OH).

後処理

  1. concentrationThe reaction mixture was then concentrated
  2. customto remove the dioxane
  3. washthen washed with EtOAc
  4. customproduct precipitation
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with H2O (20 mL)
  7. customdried at 50° C. under vacuum

出典と根拠

ORDレコード
ord-93f2eb6c74af4b30a4ee0e687ba804a0
出典データセット
uspto-grants-1997_07
特許番号
US05648368

反応ノート

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