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Diisopropylethylamine → (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl N-methyl-N-(4-trifluoromethoxybenzyl)carbamate

HRID 856183
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HRID 856183 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.[CH3:25][N:26]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][C:38]([F:41])([F:40])[F:39])=[CH:33][CH:32]=1)[C:27](Cl)=[O:28]>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:25][N:26]([CH2:30][C:31]1[CH:32]=[CH:33][C:34]([O:37][C:38]([F:39])([F:40])[F:41])=[CH:35][CH:36]=1)[C:27](=[O:28])[O:13][CH2:12][C@@:11]([OH:15])([CH3:14])[CH2:10][N:3]1[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=[C:2]1[Cl:1]
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참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 16099121(R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-methylpropane-1,2-diolHCID 23081644N-methyl-N-(4-trifluoromethoxybenzyl)carbamoylchloride

생성물 1

HCID 69481203(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl N-methyl-N-(4-trifluoromethoxybenzyl)carbamate수율 77%

시약·촉매·용매 3

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 1140Toluene용매
HCID 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 (2.16 g, 9.18 mmol), N,N-diisopropylethylamine (2.67 ml, 15.30 mmol) and 4-dimethylaminopyridine (0.19 g, 1.53 mmol) were added to a suspension of N-methyl-N-(4-trifluoromethoxybenzyl)carbamoylchloride (2.05 g, 7.65 mmol) in toluene (40 ml) followed by stirring at 100° C. for 3.5 hours. The reaction mixture was diluted with ethyl acetate, and the solution washed with 10% hydrochloric acid, 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 N-methyl-N-(4-trifluoromethoxybenzyl)carbamate (2.74 g, yield 77%) as a colorless oil.

후처리

  1. washthe solution washed with 10% hydrochloric acid
  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-391eff9df4e3470e8ef2af8594aa39c4
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07262212B2

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