Triethylamine → (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenoxy)-piperidine-1-carboxylate

HRID 856198노트

반응식

HRID 856198 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)CC)C.[F:23][C:24]([F:42])([F:41])[C:25]1[CH:40]=[CH:39][C:28]([O:29][CH:30]2[CH2:35][CH2:34][N:33]([C:36](Cl)=[O:37])[CH2:32][CH2:31]2)=[CH:27][CH:26]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:41][C:24]([F:23])([F:42])[C:25]1[CH:40]=[CH:39][C:28]([O:29][CH:30]2[CH2:31][CH2:32][N:33]([C:36]([O:13][CH2:12][C@@:11]([OH:15])([CH3:14])[CH2:10][N:3]3[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=[C:2]3[Cl:1])=[O:37])[CH2:34][CH2:35]2)=[CH:27][CH:26]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 16099121(R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-methylpropane-1,2-diolHCID 202630804-(4-Trifluoromethylphenoxy)piperidine-1-carbonylchloride

생성물 1

HCID 69481041(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenoxy)-piperidine-1-carboxylate수율 16%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

(R)-2-Chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole prepared in Example 10 (1.16 g, 4.68 mmol) and triethylamine (1.63 ml, 11.70 mmol) were added to a suspension of 4-(4-trifluoromethylphenoxy)piperidine-1-carbonylchloride (0.72 g, 2.34 mmol) in toluene (40 ml) followed by stirring at 100° C. for 2.5 hours. The reaction mixture was diluted with ethyl acetate, 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)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenoxy)-piperidine-1-carboxylate (184 mg, yield 16%) as a colorless oil.

후처리

  1. washwashed 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-3ab9c0fe20af4fe88c764f94be6e4f84
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

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