Chloromethyl Methyl Ether → (R)-2-chloro-1-(2-hydroxy-3-methoxymethoxy-2-methylpropyl)-4-nitroimidazole

HRID 856163노트

반응식

HRID 856163 반응식
[Cl:1][C:2]1[N:3]([CH2:10][C@:11]([OH:15])([CH3:14])[CH2:12][OH:13])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.C(N(CC)C(C)C)(C)C.Cl[CH2:26][O:27][CH3:28]>C(Cl)Cl>[Cl:1][C:2]1[N:3]([CH2:10][C@:11]([OH:15])([CH3:14])[CH2:12][O:13][CH2:26][O:27][CH3:28])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

참가 물질

5

반응물 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 16099121(R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-methylpropane-1,2-diol

생성물 1

HCID 69481666(R)-2-chloro-1-(2-hydroxy-3-methoxymethoxy-2-methylpropyl)-4-nitroimidazole수율 69.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(R)-2-Chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole prepared in Example 10 (7.4 g, 31 mmol) was dissolved in methylene chloride (120 ml). N,N-diisopropylethylamine (13.1 ml, 74 mmol) and chloromethylmethyl ether (7.1 ml, 74 mmol) were added to the solution followed by stirring at room temperature for 46 hours. The reaction mixture was washed with water, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1) to afford (R)-2-chloro-1-(2-hydroxy-3-methoxymethoxy-2-methylpropyl)-4-nitroimidazole (6.0 g, yield 69%) as a light yellow oil.

후처리

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1)

출처 및 근거

ORD 기록
ord-13f505ae86fc454093df0def25bc7435
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

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