Diisopropylethylamine → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-ylsulfanyl]-ethyl}-piperidine-1-carboxylic acid benzyl ester

HRID 1857639노트

반응식

HRID 1857639 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](OS(C(F)(F)F)(=O)=O)=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:29]([O-:31])=[O:30].C(N(C(C)C)CC)(C)C.[CH2:41]([O:48][C:49]([N:51]1[CH2:56][CH2:55][CH2:54][CH2:53][CH:52]1[CH2:57][CH2:58][SH:59])=[O:50])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C(OCC)(=O)C.O>[CH2:41]([O:48][C:49]([N:51]1[CH2:56][CH2:55][CH2:54][CH2:53][CH:52]1[CH2:57][CH2:58][S:59][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([N+:29]([O-:31])=[O:30])[CH:4]=2)[NH:9][C:8](=[O:12])[C:7]=1[C:13]1[CH:14]=[C:15]([CH3:20])[CH:16]=[C:17]([CH3:19])[CH:18]=1)=[O:50])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 54023713Trifluoromethanesulfonic acid 7-chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-yl esterHCID 543726122-(2-Mercaptoethyl)-piperidine-1-carboxylic acid benzyl ester

생성물 1

HCID 540282832-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-ylsulfanyl]-ethyl}-piperidine-1-carboxylic acid benzyl ester수율 21.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of trifluoromethanesulfonic acid 7-chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-yl ester (524 mg in 4 mL dry N,N-dimethylformamide) at 0° C. was added 0.38 mL diisopropylethylamine followed by 2-(2-mercaptoethyl)-piperidine-1-carboxylic acid benzyl ester (455 mg in 1 mL N,N-dimethylformamide) and the reaction allowed to warm to room temperature. After 1 hour, the mixture was diluted with ethyl acetate and water, and the layers separated. The organic portion was washed sequentially with water and brine then dried over magnesium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 7:3) gave the title compound (142 mg).

후처리

  1. customthe layers separated
  2. washThe organic portion was washed sequentially with water and brine
  3. dry with materialthen dried over magnesium sulfate
  4. customPurification of the
  5. concentrationconcentrate by flash chromatography on silica gel (hexane:ethyl acetate, 7:3)

출처 및 근거

ORD 기록
ord-56977bb378bb455fbaabcc67f416aa63
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147088

반응 노트

불러오는 중…