N-Hydroxyacetamidine → 5-{[4-(Methanesulfonyl)phenyl]methyl}-3-methyl-1,2,4-oxadiazole

HRID 2187902노트

반응식

HRID 2187902 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:27](=[N:30]O)([NH2:29])[CH3:28]>CN(C=O)C>[CH3:28][C:27]1[N:30]=[C:12]([CH2:11][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=2)[O:14][N:29]=1

참가 물질

5

반응물 3

HCID 30926N-HydroxyacetamidineHCID 682631,1'-CarbonyldiimidazoleHCID 5723454-Mesylphenylacetic acid

생성물 1

HCID 99212855-{[4-(Methanesulfonyl)phenyl]methyl}-3-methyl-1,2,4-oxadiazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-(methylsulfonyl)phenylacetic acid (15 g, 70 mmol) in DMF (300 mL) at r.t., was added carbonyldiimidazole (12.5 g, 77 mmol). After 0.5 h at r.t., acetamide oxime (5.7 g, 77 mmol) was added. After stirring the resulting mixture overnight at r.t., the mixture was heated to 120° C. for 6 h. After cooling to r.t., the mixture was quenched with H2O, and extracted with EtOAc. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (Hex:EtOAc, 1:1) yielded (3-Methyl-1,2,4-oxadiazol-5-yl) [4-(methylsulfonyl)phenyl]methane.

후처리

  1. temperaturethe mixture was heated to 120° C. for 6 h
  2. temperatureAfter cooling to r.t.
  3. customthe mixture was quenched with H2O
  4. extractionextracted with EtOAc
  5. washThe organic extracts were washed (H2O, brine)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash chromatography (Hex:EtOAc, 1:1)

출처 및 근거

ORD 기록
ord-55247a372dda474da846723c76d62d55
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06410563B1

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