Sodium methanesulfonate → (s)-2-[(s)-1-(4-Bromo-phenyl)-2,2,2-trifluoro-ethylamino]-4-methyl-pentanoic acid [(s)-1-cyano-2-(4-methanesulfonyl-phenyl)-ethyl]-amide

HRID 239862

반응식

HRID 239862 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:13][C@H:14]([C:19]([NH:21][C@H:22]([C:31]#[N:32])[CH2:23][C:24]2[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=2)=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[Na+].[CH3:34][S:35]([O-])(=[O:37])=[O:36]>CS(C)=O.CCOC(C)=O.[Cu](I)I>[C:31]([C@@H:22]([NH:21][C:19](=[O:20])[C@@H:14]([NH:13][C@@H:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[C:9]([F:12])([F:11])[F:10])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:35]([CH3:34])(=[O:37])=[O:36])=[CH:26][CH:25]=1)#[N:32]

참가 물질

6

반응물 2

HCID 638112Sodium methanesulfonateHCID 68779205N2-[(1S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl]-N-[(1S)-1-cyano-2-(4-iodophenyl)ethyl]-L-leucinamide

생성물 1

HCID 42633519(s)-2-[(s)-1-(4-Bromo-phenyl)-2,2,2-trifluoro-ethylamino]-4-methyl-pentanoic acid [(s)-1-cyano-2-(4-methanesulfonyl-phenyl)-ethyl]-amide

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To N2-[(1S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl]-N-[(1S)-1-cyano-2-(4-iodophenyl)ethyl]-L-leucinamide (1 eq) in DMSO (0.3 M) were added methane sulfonic acid sodium salt (2 eq) and copper iodide (3 eq) and the mixture was stirred at 100° C. for 2 h. The reaction mixture was cooled and diluted with EtOAc. The organic layer was washed with brine and water, dried over Na2SO4, filtered and concentrated. The crude compound was purified by automated SiO2 flash chromatography system using solvent gradient of 40% EtOAc/Hex to 100% EtOAc/Hex.

후처리

  1. temperatureThe reaction mixture was cooled
  2. washThe organic layer was washed with brine and water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude compound was purified by automated SiO2 flash chromatography system

출처 및 근거

ORD 기록
ord-53f846116d2044d497afa95b5c656f0a
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642799B2

연결된 노트

불러오는 중…