Pyridine → (S)-1-(4-Chloro-phenyl)-6-oxo-piperidine-2-carboxylic acid (3-tert-butyl-isoxazol-5-yl)-amide

HRID 336200

반응식

HRID 336200 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][C@H:9]2[C:15]([OH:17])=O)=[CH:4][CH:3]=1.[NH2:18][C:19]1[O:23][N:22]=[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:20]=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>O>[C:24]([C:21]1[CH:20]=[C:19]([NH:18][C:15]([C@@H:9]2[CH2:10][CH2:11][CH2:12][C:13](=[O:14])[N:8]2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:17])[O:23][N:22]=1)([CH3:27])([CH3:26])[CH3:25]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 20956943-Tert-butyl-1,2-oxazol-5-amineHCID 42127104(S)-1-(4-Chloro-phenyl)-6-oxo-piperidine-2-carboxylic acid

생성물 1

HCID 58563752(S)-1-(4-Chloro-phenyl)-6-oxo-piperidine-2-carboxylic acid (3-tert-butyl-isoxazol-5-yl)-amide

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

To a cold slurry of (S)-1-(4-Chloro-phenyl)-6-oxo-piperidine-2-carboxylic acid (0.2 g; 0.788 mmol) and 5-amino-3-tert-butylisoxazole (0.110 g; 0.788 mmol) in pyridine (0.956 mL; 11.820 mmol) is added phosphorous oxychloride (0.088 mL; 0.946 mmol). The mixture is stirred at 0° C. for 30 minutes and then diluted with water and extracted with ethyl acetate several times. The organics are combined and washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by preparative HPLC affords title compound, m/z 376 [M+H+].

후처리

  1. extractionextracted with ethyl acetate several times
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative HPLC

출처 및 근거

ORD 기록
ord-cc60fa4f3eba4880b745e202d0cd6112
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889670B2

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