Imidazole → N-[5-((R)-2-Azido-1-triethylsilyloxyethyl)-2-benzyloxyphenyl]methanesulfonamide

HRID 2220652노트

반응식

HRID 2220652 반응식
N1C=CN=C1.[CH2:6]([Si:8](Cl)([CH2:11][CH3:12])[CH2:9][CH3:10])[CH3:7].[N:14]([CH2:17][C@@H:18]([C:20]1[CH:21]=[CH:22][C:23]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:25]=1)[OH:19])=[N+:15]=[N-:16].O>CN(C)C=O>[N:14]([CH2:17][C@@H:18]([C:20]1[CH:21]=[CH:22][C:23]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:24]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH:25]=1)[O:19][Si:8]([CH2:11][CH3:12])([CH2:9][CH3:10])[CH2:6][CH3:7])=[N+:15]=[N-:16]

참가 물질

6

반응물 4

HCID 795Imidazole2회HCID 962WaterHCID 13819Chlorotriethylsilane2회HCID 86611776N-[5-((R)-2-azido-1-hydroxyethyl)-2-benzyloxyphenyl]methanesulfonamide

생성물 1

HCID 86611775N-[5-((R)-2-Azido-1-triethylsilyloxyethyl)-2-benzyloxyphenyl]methanesulfonamide수율 85.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Imidazole (0.46 g) and triethylsilyl chloride (0.82 g) were added to a solution of N-[5-((R)-2-azido-1-hydroxyethyl)-2-benzyloxyphenyl]methanesulfonamide (1.64 g) in N,N-dimethylformamide (20 mL), and the mixture was stirred at room temperature for 12 hrs. Imidazole (0.15 g) and triethylsilyl chloride (0.21 g) were added to the reaction mixture. After being stirred for additional 3 hrs, water was added to the mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium-pressure silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1) to afford the title compound (1.84 g).

후처리

  1. stirringAfter being stirred for additional 3 hrs
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by medium-pressure silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-66c99e018df54774a978a365acd46240
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417169B2

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