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 11682노트

반응식

HRID 11682 반응식
[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]

참가 물질

6

반응물 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

생성물 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 Ester수율 44.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-749a9b298e704c3cbd3759170ce98838
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098212B2

반응 노트

불러오는 중…