Sodium Hydroxide → 5-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

HRID 2166999노트

반응식

HRID 2166999 반응식
[O-]Cl.[Na+].[OH-].[Na+].[F:6][C:7]([F:22])([F:21])[CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]([CH:18]=[N:19][OH:20])=[CH:15][C:16]=1[CH3:17])=[O:11].[Cl:23][C:24]1[CH:29]=[C:28]([C:30]([C:32]([F:35])([F:34])[F:33])=[CH2:31])[CH:27]=[C:26]([Cl:36])[CH:25]=1>C1COCC1.C(OCC)C>[F:22][C:7]([F:6])([F:21])[CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]([C:18]2[CH2:31][C:30]([C:28]3[CH:27]=[C:26]([Cl:36])[CH:25]=[C:24]([Cl:23])[CH:29]=3)([C:32]([F:33])([F:35])[F:34])[O:20][N:19]=2)=[CH:15][C:16]=1[CH3:17])=[O:11]

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 23665760Sodium HypochloriteHCID 866580365-(Hydroxyimino-methyl)-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

생성물 1

HCID 866580375-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide수율 15.7%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

Chlorox (4%, 1.02 nil) and NaOH (1N, 0.1 ml) are premixed and then added to a solution of 5-(hydroxyimino-methyl)-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide (200 mg) and 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (170 mg, example 1, Step A) in THF (3 ml) and diethyl ether (3 ml) at 5° C. The cold bath is then removed. After 21 hours, water is added and the reaction mixture is extracted three times with ethyl acetate. The organic phases are combined, dried over Na2SO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide (56 mg) as light yellow oil. MS (HPLC/MS): 505 (MH+). Retention time: 4.38 min.

후처리

  1. customThe cold bath is then removed
  2. additionwater is added
  3. extractionthe reaction mixture is extracted three times with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified on a semi-preparative HPLC

출처 및 근거

ORD 기록
ord-084c885680cc44c89b6d162838f7e8b6
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09044389B2

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