Trifluoroacetic acid → C-{2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-yl}-methylamine

HRID 68580

반응식

HRID 68580 반응식
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH2:15][C:16]1[CH:20]=[C:19]([C:21]2[CH2:25][C:24]([C:30]3[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=3)([C:26]([F:29])([F:28])[F:27])[O:23][N:22]=2)[O:18][C:17]=1[CH3:39])(C)(C)C.[OH-].[Na+]>ClCCl>[CH3:39][C:17]1[O:18][C:19]([C:21]2[CH2:25][C:24]([C:30]3[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=3)([C:26]([F:28])([F:27])[F:29])[O:23][N:22]=2)=[CH:20][C:16]=1[CH2:15][NH2:14]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86706654{2-Methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-ylmethyl}-carbamic acid tert-butyl ester

생성물 1

HCID 86706655C-{2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-yl}-methylamine수율 98.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid (6.0 ml) is added to a solution of {2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-ylmethyl}-carbamic acid tert-butyl ester (2.05 g) in dichloromethane (20 ml). After 45 min at room temperature, an aqueous solution of NaOH (2M) is added until pH 12 is reached and the reaction mixture is extracted three times with dichloromethane. The combined organic phases are washed with a saturated solution of NaCl, dried over Na2SO4 and concentrated in vacuo to yield C-{2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-yl}-methylamine (1.64 g, compound 2.5 in Table 2) as a light yellow foam. The crude product obtained is used without further purification. MS (HPLC/MS): 410 (MH), Retention time: 1.27 min.

후처리

  1. extractionthe reaction mixture is extracted three times with dichloromethane
  2. washThe combined organic phases are washed with a saturated solution of NaCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a3d259fbdfa2492fa1f1c34f1efc80a0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822466B2

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