Phosphorus oxychloride → (S)-1-(4-Chloro-phenyl)-azetidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

HRID 389864노트

반응식

HRID 389864 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:11][CH2:10][C@H:9]2[C:12]([OH:14])=O)=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[O:18][N:17]=1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1.C(OCC)(=O)C>[C:21]([C:19]1[O:18][N:17]=[C:16]([NH:15][C:12]([C@@H:9]2[CH2:10][CH2:11][N:8]2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:14])[CH:20]=1)([CH3:24])([CH3:23])[CH3:22]

참가 물질

6

반응물 3

HCID 24813Phosphorus oxychlorideHCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-HCID 67284015(S)-1-(4-Chloro-phenyl)-azetidine-2-carboxylic acid

생성물 1

HCID 49847935(S)-1-(4-Chloro-phenyl)-azetidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

To a cold solution (0° C.) of (S)-1-(4-Chloro-phenyl)-azetidine-2-carboxylic acid (100 mg; 0.472 mmol) and 3-amino-5-t-butylisoxazole (66 mg; 0.472 mmol) in pyridine (1.5 mL) is added phosphorus oxychloride (0.043 m; 0.48 mmol). The reaction mixture is stirred at room temperature for 18 hours. After this time, the reaction mixture is diluted with ethyl acetate and washed with diluted NH4Cl aqueous solution then brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using ethyl acetate/hexanes provides the title compound, m/z 334 [M+H+].

후처리

  1. washwashed with diluted NH4Cl aqueous solution
  2. dry with materialbrine, dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-b2cc651ec39947a2ba3eca88ae25c82e
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383615B2

반응 노트

불러오는 중…