2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-(3-allyloxycarbonylphenylcarbamoyl)pyrrolidine

HRID 341875ノート

反応式

HRID 341875 の反応式
[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[C@H:7]([C:16]([OH:18])=O)[CH2:6]1)(=[O:3])[CH3:2].[NH2:19][C:20]1[CH:21]=[C:22]([CH:29]=[CH:30][CH:31]=1)[C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24].C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[C@H:7]([C:16](=[O:18])[NH:19][C:20]2[CH:31]=[CH:30][CH:29]=[C:22]([C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24])[CH:21]=2)[CH2:6]1)(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 15299255(2S,4S)-4-Acetylthio-1-allyloxycarbonyl-2-carboxypyrrolidineHCID 18930599Allyl 3-aminobenzoate

生成物 1

HCID 53680604(2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-(3-allyloxycarbonylphenylcarbamoyl)pyrrolidine収率 101.1%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(2S,4S)-4-Acetylthio-1-allyloxycarbonyl-2-carboxypyrrolidine (2.54 g, 9.3 mM), allyl 3-aminobenzoate (1.5 g, 8.5 mNM), and 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (2.72 g, 11 mM) were dissolved in toluene (50 ml) and stirred for 18 hours at ambient temperature. The reaction mixture was diluted with ethyl acetate (150 ml) and washed with 2M HCl (3 by 30 ml), water, saturated NaHCO3, and brine. Drying over MgSO4 and evaporation gave (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-(3-allyloxycarbonylphenylcarbamoyl)pyrrolidine as a gum (3.7 g, 100%) in a state sufficiently pure for further work. Nmr (CDCl3): δ 2.32 (s, 3H); 2.60 (br, 2H); 3.40 (dd, 1H); 4.03 (quintet, 1H); 4.13 (dd, 1H); 4.57 (t, 1H); 4.66 (dm, 2H); 4.82 (dt, 2H); 5.23-5.46 (m, 4H); 5.86-6.12 (m, 2H); 7.41 (t, 1H); 7.82 (d, 1H); 7.91 (d, 1H); 8.07 (t, 1H); 9.18 (br, 1H).

後処理

  1. washwashed with 2M HCl (3 by 30 ml), water, saturated NaHCO3, and brine
  2. dry with materialDrying over MgSO4 and evaporation

出典と根拠

ORDレコード
ord-e4adccb44e25482089d3e76677ad4cce
出典データセット
uspto-grants-1999_01
特許番号
US05856321

反応ノート

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