Potassium Carbonate → 3-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acrylic Acid Ethyl Ester

HRID 11682ノート

反応式

HRID 11682 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=O)[C:5]([O:8][CH2:9][C:10]([N:12]2[CH2:17][CH:16]([CH3:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:14][CH:13]2[CH3:27])=[O:11])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:36]([O-:39])(=[O:38])[CH3:37].[CH2:40]([PH+](CC)CC)[CH3:41]>C(O)C.O>[CH2:40]([O:38][C:36](=[O:39])[CH:37]=[CH:28][C:4]1[C:5]([O:8][CH2:9][C:10]([N:12]2[CH2:17][C@H:16]([CH3:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:14][C@H:13]2[CH3:27])=[O:11])=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH3:41]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 219733105-Chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridine-3-carbaldehydeHCID 21973468Triethylphosphonium acetate

生成物 1

HCID 696553743-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acrylic Acid Ethyl Ester収率 44.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a 0° C. solution of 5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridine-3-carbaldehyde (0.200 g, 0.47 mmol) in ethanol (5 mL) was added potassium carbonate (0.131 g, 0.95 mmol) in water (0.30 mL) and triethyl phosphonium acetate (0.21 g, 0.19 mL). The reaction mixture was warmed to room temperature over 48 hours, filtered through celite, the filter cake was washed with ethanol and concentrated in vacuo. Purification via chromatography on silica gel gave the title compound (0.102 g).

後処理

  1. filtrationfiltered through celite
  2. washthe filter cake was washed with ethanol
  3. concentrationconcentrated in vacuo
  4. customPurification via chromatography on silica gel

出典と根拠

ORDレコード
ord-749a9b298e704c3cbd3759170ce98838
出典データセット
uspto-grants-2006_08
特許番号
US07098212B2

反応ノート

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