Methyl iodide → N-[4-methoxybenzenesulfonyl]-(D)-asparagine methyl ester

HRID 2209710

반응식

HRID 2209710 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C@@H:13]([C:18]([OH:20])=[O:19])[CH2:14][C:15](=[O:17])[NH2:16])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[C:21](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C)C=O.[Cl-].[NH4+]>[CH3:21][O:19][C:18](=[O:20])[C@@H:13]([CH2:14][C:15](=[O:17])[NH2:16])[NH:12][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 27014145N-[4-methoxybenzenesulfonyl]-(D)-asparagine

생성물 1

HCID 70060643N-[4-methoxybenzenesulfonyl]-(D)-asparagine methyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 25517Ammonium Chloride용매

실험 절차

N-[4-methoxybenzenesulfonyl]-(D)-asparagine (10.1 g, 33.3 mmol) is dissolved in dimethylformamide (167.0 mL). Cesium carbonate (5.43 g, 16.66 mmol) is added, followed by the addition of methyl iodide (2.22 mL, 33.3 mmol), and the reaction is stirred overnight. The reaction is then diluted with saturated ammonium chloride (366.0 mL), and extracted well with ethyl acetate. The combined organic extracts are washed with brine, dried (Na2SO4), and the solvent is evaporated. The crude product is recrystallized from toluene to provide N-[4-methoxybenzenesulfonyl]-(D)-asparagine methyl ester.

후처리

  1. extractionextracted well with ethyl acetate
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent is evaporated
  5. customThe crude product is recrystallized from toluene

출처 및 근거

ORD 기록
ord-43f63c5458e4412895226e317caeca8b
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05455258

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