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1,10-Phenanthroline → 3-Benzooxazol-2-yl-azetidine-1-carboxylic acid benzyl ester

HRID 528747
ノート
印刷プレビュー

反応式

HRID 528747 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15](=[O:24])[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2I)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])(O)=O.[Na+]>COCCOC.Cl.[Cu]I.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15]2[O:24][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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

9

反応物 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 674562543-(2-Iodo-phenylcarbamoyl)-azetidine-1-carboxylic acid benzyl ester

生成物 1

HCID 674541823-Benzooxazol-2-yl-azetidine-1-carboxylic acid benzyl ester

試薬・触媒・溶媒 4

HCID 313
Hydrochloric Acid
触媒
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 962Water溶媒
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

To 195 mg (0.45 mmol) 3-(2-iodo-phenylcarbamoyl)-azetidine-1-carboxylic acid benzyl ester in 4.5 mL DME in a sealed tube under nitrogen were added 291 mg (0.89 mmol) Cs2CO3, 8.1 mg (44.6 μmol) 1,10-phenanthroline, 4.3 mg (22.3 μmol) CuI, and the mixture was heated at 90° C. for 16 hours. After cooling to room temperature, 5 mL H2O was added followed by 4 drops 1 M HCl, 5 mL NaHCO3 and the mixture was extracted with DCM (3×10 mL). The organic layers were combined and dried with Na2SO4. After filtration and evaporation of the solvent the product was purified by preparative HPLC.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with DCM (3×10 mL)
  3. dry with materialdried with Na2SO4
  4. filtrationAfter filtration and evaporation of the solvent the product
  5. customwas purified by preparative HPLC

出典と根拠

ORDレコード
ord-5cd5c7b326da43ec8c639dd15612c781
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09346816B2

反応ノート

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