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[(2R)-2-methyloxiranyl]methyl 4-methylbenzene-sulfonate → (R)-2-chloro-1-[2-hydroxy-2-methyl-3-(4-methylbenzenesulfonyloxy)propyl]-4-nitroimidazole

HRID 856154
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HRID 856154 반응식
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:20][CH2:21][C@@:22]2([CH3:25])[CH2:24][O:23]2)(=[O:19])=[O:18])=[CH:13][CH:12]=1>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[N:3]([CH2:25][C@:22]([OH:23])([CH3:24])[CH2:21][O:20][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:10])=[CH:12][CH:13]=2)(=[O:19])=[O:18])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1
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참가 물질

5

반응물 2

HCID 10900803[(2R)-2-methyloxiranyl]methyl 4-methylbenzene-sulfonateHCID 178526855HCID 178526855, 화합물

생성물 1

HCID 86604802(R)-2-chloro-1-[2-hydroxy-2-methyl-3-(4-methylbenzenesulfonyloxy)propyl]-4-nitroimidazole수율 43%

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 6342Acetonitrile
용매

실험 절차

2-Chloro-4-nitro-1H-imidazole (18.4 g, 125 mmol) and (R)-2-methyloxiran-2-ylmethyl 4-methylbenzene sulfonate (36.2 g, 149 mmol) were suspended in acetonitrile (150 ml). Benzyl(triethyl)ammonium chloride (5.7 g, 25 mmol) was added to the suspension, and the resulting mixture was stirred under reflux for 8 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=20/1) to afford (R)-2-chloro-1-[2-hydroxy-2-methyl-3-(4-methylbenzenesulfonyloxy)propyl]-4-nitroimidazole (20.1 g, 43%) as a white amorphous form.

후처리

  1. temperatureunder reflux for 8 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=20/1)

출처 및 근거

ORD 기록
ord-7817b2a2dad14a5a99621ce26d7745e1
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07262212B2

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