4-Chlorophenyl Isocyanate → (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-chlorophenylcarbamate

HRID 856182노트

반응식

HRID 856182 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:18][C:19]1[N:20]([CH2:27][C@:28]([OH:32])([CH3:31])[CH2:29][OH:30])[CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[N:23]=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[O:30][CH2:29][C@@:28]([OH:32])([CH3:31])[CH2:27][N:20]2[CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[N:23]=[C:19]2[Cl:18])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 16099121(R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-methylpropane-1,2-diol

생성물 1

HCID 69481886(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-chlorophenylcarbamate수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A THF solution (15 ml) of 4-chlorophenylisocyanate (1.3 g, 85 mmol) and triethylamine (0.1 ml) were added to a suspension of (R)-2-chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole prepared in Example 10 (1.5 g, 6.5 mmol) in THF (30 ml) followed by stirring at room temperature for 19 hours. Insoluble matters were removed by filtration, and the filtrate was 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-chlorophenylcarbamate (2.1 g, yield 83%) as a white solid.

후처리

  1. customInsoluble matters were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1)

출처 및 근거

ORD 기록
ord-96f878a971954b01acbb7224b8b93bd5
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

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