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

HRID 1972254노트

반응식

HRID 1972254 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

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온도
110 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-cf706bf919a247b6a5484cd9716f50ea
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431607B2

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