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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
ノート
印刷プレビュー

反応式

HRID 1888324 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f0e08713e95f49609e504eddfe8c31a2
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08501793B2

反応ノート

読み込み中…

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