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Potassium Carbonate → Methyl 2-(5-(2-(azetidin-1-yl)ethoxy)-2-(benzyloxy)benzamido)-4-phenylbenzoate

HRID 454695
ノート
印刷プレビュー

反応式

HRID 454695 の反応式
C(=O)([O-])[O-].[K+].[K+].Cl.[NH:8]1[CH2:11][CH2:10][CH2:9]1.CN1CCCC1=O.[CH2:19]([O:26][C:27]1[CH:51]=[CH:50][C:49]([O:52][CH2:53][CH2:54]Br)=[CH:48][C:28]=1[C:29]([NH:31][C:32]1[CH:41]=[C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:39]=[CH:38][C:33]=1[C:34]([O:36][CH3:37])=[O:35])=[O:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C.O>[N:8]1([CH2:54][CH2:53][O:52][C:49]2[CH:50]=[CH:51][C:27]([O:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:28]([CH:48]=2)[C:29]([NH:31][C:32]2[CH:41]=[C:40]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:39]=[CH:38][C:33]=2[C:34]([O:36][CH3:37])=[O:35])=[O:30])[CH2:11][CH2:10][CH2:9]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

7

反応物 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 12308726Azetidine hydrochlorideHCID 66990627Methyl 2-(2-(benzyloxy)-5-(2-bromoethoxy)benzamido)-4-phenylbenzoate

生成物 1

HCID 66990372Methyl 2-(5-(2-(azetidin-1-yl)ethoxy)-2-(benzyloxy)benzamido)-4-phenylbenzoate収率 36.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

Potassium carbonate (0.15 g) and azetidine hydrochloride (0.046 g) were added to a 1-methyl-2-pyrrolidone (1.3 mL) solution of methyl 2-(2-(benzyloxy)-5-(2-bromoethoxy)benzamido)-4-phenylbenzoate (0.25 g), followed by stirring at 90° C. for 45 minutes. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol] to obtain 0.088 g of methyl 2-(5-(2-(azetidin-1-yl)ethoxy)-2-(benzyloxy)benzamido)-4-phenylbenzoate as a light yellow oily substance.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol]

出典と根拠

ORDレコード
ord-ee6c4b78092441868ea100df8f362ff1
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08492582B2

反応ノート

読み込み中…

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