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Ethyl bromopyruvate → Ethyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylate

HRID 1425078
ノート
印刷プレビュー

反応式

HRID 1425078 の反応式
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)(O)[O-].[Na+].[C:15]([N:18]1[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:20]([O:35][CH3:36])[CH2:19]1)(=[O:17])[NH2:16]>C1COCC1>[CH2:27]([O:26][C:25]([NH:24][C@H:21]1[CH2:22][CH2:23][N:18]([C:15]2[O:17][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:16]=2)[CH2:19][C@H:20]1[O:35][CH3:36])=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 131730860cis(+/-)-Benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate

生成物 1

HCID 86648578Ethyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylate収率 79.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

Ethyl bromopyruvate (2.93 g, 15 mmol) and sodium bicarbonate (2.10 g, 25 mmol) were added to a solution of cis(±)-benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate obtained in Example (103b) (1.4 g, 4.56 mmol) in THF (30 mL), and the mixture was stirred at 70° C. for three hours. The insoluble matter was filtered off, followed by dilution with ethyl acetate. This was washed with water and brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1, 2/1, 4/1) to obtain 1.46 g of the title compound as a colorless solid (79%).

後処理

  1. filtrationThe insoluble matter was filtered off
  2. washThis was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1, 2/1, 4/1)

出典と根拠

ORDレコード
ord-4688cff090194cdf8ef879d47c673b92
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08927588B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート