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Imidazole → ethyl 2-{[(2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-oxo-1-pyrrolidinyl]methyl}-1,3-thiazole-4-carboxylate

HRID 1888324
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HRID 1888324 반응식
[Si:1]([O:8][CH2:9][C@H:10]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]1[CH2:16][C:17](=[S:19])[NH2:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[CH2:21][C:22](=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24].N1C=CN=C1.[Si](Cl)(C(C)(C)C)(C)C>CN(C)C=O.O.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][C@H:10]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]1[CH2:16][C:17]1[S:19][CH:21]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:18]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 66144Ethyl bromopyruvateHCID 866500602-[(2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-oxo-1-pyrrolidinyl]ethanethioamide

생성물 1

HCID 66857942ethyl 2-{[(2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-oxo-1-pyrrolidinyl]methyl}-1,3-thiazole-4-carboxylate

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of the compound 68 (4.50 g) in dimethylformamide (15.0 mL) was ethyl bromopyruvate (2.33 mL) at 0° C. and the solution was stirred at room temperature for 2 Hours. To the reaction solution were added imidazole (4.08 g) and tert-butyldimethylsilyl chloride (4.52 g) at 0° C. and the solution was stirred at room temperature for 2 Hours. To the reaction solution were added ethyl acetate and water and then the solution was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with an aqueous saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:2→2:3) to give the title compound (4.75 g) having the following physical data.

후처리

  1. customat 0° C.
  2. stirringthe solution was stirred at room temperature for 2 Hours
  3. customthe solution was separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with an aqueous saturated sodium bicarbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:2→2:3)

출처 및 근거

ORD 기록
ord-f0e08713e95f49609e504eddfe8c31a2
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08501793B2

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