p-Toluenesulfonic acid → tert-butyl 2-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxyacetate

HRID 1022839노트

반응식

HRID 1022839 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:23]([F:26])([F:25])[F:24])[O:13][N:12]=[C:11]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[C:16]([CH3:22])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:27]([O:31][C:32](=[O:36])[CH2:33][O:34][NH2:35])([CH3:30])([CH3:29])[CH3:28].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:27]([O:31][C:32](=[O:36])[CH2:33][O:34]/[N:35]=[CH:18]/[C:17]1[CH:20]=[CH:21][C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)([C:23]([F:26])([F:24])[F:25])[O:13][N:12]=2)=[CH:15][C:16]=1[CH3:22])([CH3:30])([CH3:29])[CH3:28]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 12919121tert-Butyl (aminooxy)acetateHCID 866585204-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde2회

생성물 1

HCID 87403035tert-butyl 2-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxyacetate수율 56%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde (i.e. the product of Step 1, Example 1, 1.00 g), amino-oxyacetic-acid-tert-butyl-ester (403 mg), p-toluene sulfonic acid (43 mg) and toluene (20 mL) were heated to reflux for 30 min. After cooling, the mixture was washed with water, and the organic layer was dried over Na2SO4. After evaporation the residue was purified by flash chromatography on silica gel to yield the title compound (745 mg, 56%)

후처리

  1. temperaturewere heated
  2. temperatureto reflux for 30 min
  3. temperatureAfter cooling
  4. washthe mixture was washed with water
  5. dry with materialthe organic layer was dried over Na2SO4
  6. customAfter evaporation the residue
  7. customwas purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-4080817f084d4468b3caecc65252dbca
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722673B2

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