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

HRID 341878ノート

反応式

HRID 341878 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6].[C:14]([S:17][CH:18]1[CH2:22][N:21]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[CH:20]([C:36](O)=[O:37])[CH2:19]1)(=[O:16])[CH3:15].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1>C1(C)C=CC=CC=1.CCOC(C)=O>[C:14]([S:17][C@@H:18]1[CH2:22][N:21]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[C@H:20]([C:36](=[O:37])[NH:1][C:2]2[CH:13]=[CH:12][CH:11]=[C:4]([C:5]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6])[CH:3]=2)[CH2:19]1)(=[O:16])[CH3:15]

参加物

6

反応物 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 135043244-Acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-carboxypyrrolidineHCID 18930599Allyl 3-aminobenzoate

生成物 1

HCID 53813961(2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(3-allyloxycarbonylphenylcarbamoyl)pyrrolidine収率 85.6%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The above allyl 3-aminobenzoate (26.6 g, 0.15M) was condensed with 4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-carboxypyrrolidine (55.2 g, 0.15M) by suspension in toluene (750 ml) and addition of EEDQ (44.5 g, 0.18M). The mixture was stirred overnight, diluted with EtOAc (2 l) and washed with dilute HCl, water and brine. The EtOAc phase was dried and evaporated, and the residue recrystallised from ethanol giving (2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(3-allyloxycarbonylphenylcarbamoyl)pyrrolidine (67.7 g). Nmr (DHSO-d6): δ 1.93 (quintet, 1H); 2.9 (m, 1H); 3.35 (m, 1H); 3.91-4.14 (m, 2H); 4.49 (quintet, 1H); 4.81 (dd, 2H); 5.22 (dd, 2H); 5.2-5.44 (m, 2H); 5.95-6.10 (m, 1H); 7.47 (d, 2H); 7.66 (t, 2H); 7.8-7.93 (m, 2H); 8.18-8.3 (m, 2H); 10.31 (s, 1H).

後処理

  1. washwashed with dilute HCl, water and brine
  2. dry with materialThe EtOAc phase was dried
  3. customevaporated
  4. customthe residue recrystallised from ethanol

出典と根拠

ORDレコード
ord-21dbb46a5e994df98b5457107554e612
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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