Hydrochloric Acid → Methyl [4-(4-chlorophenyl)-3-(cyclopropylmethyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

HRID 660910ノート

反応式

HRID 660910 の反応式
[CH3:1][O:2][C:3](=[O:18])[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[NH:7][C:6]1=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:26]1([CH3:29])[CH2:28][CH2:27]1.Cl>CC(C)=O.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:18])[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[N:7]([CH2:29][CH:26]2[CH2:28][CH2:27]2)[C:6]1=[O:17]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 148649461-Bromo-1-methylcyclopropaneHCID 58012289Methyl[4-(4-chlorophenyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

生成物 1

HCID 58012093Methyl [4-(4-chlorophenyl)-3-(cyclopropylmethyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

300 mg (1.13 mmol) of the compound from Example 232A together with 1.10 g (3.38 mmol) of caesium carbonate are placed in 12 ml acetone and treated with 456 mg (3.38 mmol) of bromo-methylcyclopropane. This is stirred for 2 hrs at 50° C. The reaction mixture is then diluted with 10 ml each of ethyl acetate and water and acidified with 1 N hydrochloric acid. The phases are separated and the aqueous phase is once again extracted with 10 ml ethyl acetate. The combined organic phases are dried over sodium sulphate, filtered and concentrated in vacuo. Further purification is effected by preparative HPLC [Method 10]. 60 mg (17% of theory) of the target compound are thus obtained.

後処理

  1. customThe phases are separated
  2. extractionthe aqueous phase is once again extracted with 10 ml ethyl acetate
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customFurther purification
  7. custom60 mg (17% of theory) of the target compound are thus obtained

出典と根拠

ORDレコード
ord-a3356781a4db4369ac38d105ea11161e
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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