1,2-Diaminocyclohexane → 3-[4-(4-Chlorophenoxy)phenyl]-4-(3-methoxyphenyl)-oxazolidin-2-one

HRID 1972254ノート

反応式

HRID 1972254 の反応式
C(O[C:9](=[O:22])[NH:10][CH:11]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)[CH2:12][OH:13])C1C=CC=CC=1.[Cl:23][C:24]1[CH:37]=[CH:36][C:27]([O:28][C:29]2[CH:34]=[CH:33][C:32](I)=[CH:31][CH:30]=2)=[CH:26][CH:25]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(N)CCCCC1N>[Cu]I.CN(C=O)C>[Cl:23][C:24]1[CH:37]=[CH:36][C:27]([O:28][C:29]2[CH:34]=[CH:33][C:32]([N:10]3[CH:11]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=4)[CH2:12][O:13][C:9]3=[O:22])=[CH:31][CH:30]=2)=[CH:26][CH:25]=1

参加物

7

反応物 4

HCID 46101,2-DiaminocyclohexaneHCID 62657Potassium Phosphate, TribasicHCID 193519901-Chloro-4-(4-iodophenoxy)benzeneHCID 68702649benzyl N-[2-hydroxy-1-(3-methoxyphenyl)ethyl]carbamate

生成物 1

HCID 687060693-[4-(4-Chlorophenoxy)phenyl]-4-(3-methoxyphenyl)-oxazolidin-2-one収率 76.8%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

To a dry round bottom flask is added [2-hydroxy-1-(3-methoxy-phenyl)ethyl]-carbamic acid benzyl ester (300 mg, 1 mmol), 1-(4-chlorophenoxy)-4-iodobenzene (330 mg, 1 mmol), K3PO4 (210 mg), 1,2-cyclohexanediamine (15 μL) and CuI (20 mg), and DMF (5 mL). The mixture is evacuated and back-filled with nitrogen three times. The reaction mixture is heated to 110° C. for 7 h. The reaction is then cooled to room temperature, diluted with EtOAc (50 mL), washed with 1N HCl, and brine, subsequently dried over MgSO4, filtered, and concentrated to give the crude product, which is purified by flash chromatography on silica gel (EtOAc/Hex: 1/2) to provide 3-[4-(4-chlorophenoxy)phenyl]-4-(3-methoxyphenyl)-oxazolidin-2-one (304 mg).

後処理

  1. customThe mixture is evacuated
  2. additionback-filled with nitrogen three times
  3. temperatureThe reaction is then cooled to room temperature
  4. additiondiluted with EtOAc (50 mL)
  5. washwashed with 1N HCl, and brine
  6. dry with materialsubsequently dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product, which
  10. customis purified by flash chromatography on silica gel (EtOAc/Hex: 1/2)

出典と根拠

ORDレコード
ord-cf706bf919a247b6a5484cd9716f50ea
出典データセット
uspto-grants-2013_04
特許番号
US08431607B2

反応ノート

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