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 1857639ノート

反応式

HRID 1857639 の反応式
[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

参加物

6

反応物 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

生成物 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 ester収率 21.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-56977bb378bb455fbaabcc67f416aa63
出典データセット
uspto-grants-2000_11
特許番号
US06147088

反応ノート

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