Potassium Carbonate → Ethyl 3-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}benzoate

HRID 43890

反応式

HRID 43890 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18].N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C.[Cu]I>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][N:11]([C:14]2[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 143542Ethyl 3-iodobenzoateHCID 145742L-ProlineHCID 15194053-Aminoazetidine, 3-BOC protected

生成物 1

HCID 68405850Ethyl 3-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}benzoate収率 57.2%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

A suspension of 3-tert-butoxycarbonylaminoazetidine (300 mg, 1.74 mmol), ethyl 3-iodobenzoate (721 mg, 2.61 mmol) and copper (I) iodide (66 mg, 0.35 mmol), proline (80 mg, 0.70 mmol) and potassium carbonate (721 mg, 5.22 mmol) in DMSO was stirred at 120° C. for two hours. The reaction solution was diluted with ethyl acetate and then filtered. The filtrate was washed with brine and then dried over anhydrous magnesium sulfate. Following filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1) to obtain 319 mg of the title compound as a milk white solid (57%).

後処理

  1. filtrationfiltered
  2. washThe filtrate was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-5a04a1605eb34951a9345797ad1dceed
出典データセット
uspto-grants-2013_09
特許番号
US08536197B2

関連ノート

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