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

HRID 36644

반응식

HRID 36644 반응식
[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

참가 물질

6

반응물 4

HCID 6267(-)-AsparagineHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium Hydroxide2회HCID 312751,4-Dioxane

생성물 1

HCID 10754635N-Phenysulfonyl-L-asparagine

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
0 °C

실험 절차

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 1 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 3 with conc. 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 22-1 as a white solid.

후처리

  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

출처 및 근거

ORD 기록
ord-4324c719dd004167b36a71ddfbff7803
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05416099

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