Ethyl 2-chloroacetoacetate → Ethyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-oxazole-5-carboxylate

HRID 1425095ノート

反応式

HRID 1425095 の反応式
[C:1]([N:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:6]([O:21][CH3:22])[CH2:5]1)(=[O:3])[NH2:2].Cl[CH:24]([C:30]([CH3:32])=O)[C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:13]([O:12][C:11]([NH:10][C@H:7]1[CH2:8][CH2:9][N:4]([C:1]2[O:3][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:30]([CH3:32])[N:2]=2)[CH2:5][C@H:6]1[O:21][CH3:22])=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

5

反応物 3

HCID 11858Ethyl 2-chloroacetoacetateHCID 516892Sodium BicarbonateHCID 131730860cis(+/-)-Benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate

生成物 1

HCID 86648586Ethyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-oxazole-5-carboxylate収率 31.1%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

cis(±)-Benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate obtained in Example (103b) (0.92 g, 3 mmol), ethyl α-chloroacetoacetate (3.29 g, 20 mmol) and sodium bicarbonate (0.84 g, 10 mmol) were stirred at 120° C. for three hours. The reaction solution was diluted with ethyl acetate, washed with water and brine, and dried over anhydrous magnesium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 2/1, 4/1) to obtain 0.39 g of the title compound as a light brown solid (27%).

後処理

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentration under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 2/1, 4/1)

出典と根拠

ORDレコード
ord-f8fe519eb1864a579b4cb32bb62e93e4
出典データセット
uspto-grants-2015_01
特許番号
US08927588B2

反応ノート

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