Cesium carbonate → Ethyl2-[4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-propionate

HRID 660871ノート

反応式

HRID 660871 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[NH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH:13]3[CH2:14][CH2:15]3)[C:11](=[O:16])[N:10]([CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:9]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 79040Ethyl 2-bromopropionateHCID 580118325-(4-chlorophenyl)-1-cyclopropyl-1,3-dihydro-2H-imidazol-2-one

生成物 1

HCID 58011824Ethyl2-[4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-propionate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

500 mg (2.13 mmol) of 5-(4-chlorophenyl)-1-cyclopropyl-1,3-dihydro-2H-imidazol-2-one from Example 118A are dissolved in 5 ml acetonitrile and treated with 386 mg (2.13 mmol) of ethyl 2-bromopropionate and 1388 mg (4.26 mmol) of caesium carbonate. The mixture is stirred under reflux overnight. It is then concentrated, the residue is partitioned between dichloromethane and water, the organic phase is separated, and this is dried over sodium sulphate and again concentrated. The crude product is purified by flash chromatography on silica gel (eluent: first dichloromethane, then dichloromethane/methanol 200:1→100:1) and thus yields 338 mg (45% of theory) of the target compound.

後処理

  1. temperatureunder reflux overnight
  2. concentrationIt is then concentrated
  3. customthe residue is partitioned between dichloromethane and water
  4. customthe organic phase is separated
  5. dry with materialthis is dried over sodium sulphate
  6. concentrationagain concentrated
  7. customThe crude product is purified by flash chromatography on silica gel (eluent

出典と根拠

ORDレコード
ord-303ae6f527f44bcbabf0f85dd680a8c5
出典データセット
uspto-grants-2011_12
特許番号
US08084481B2

反応ノート

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