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1-({2-(Hex-5-enyl-methyl-carbamoyl)-4-[2-(4-isopropyl-thiazol-2-yl)-7-methoxy-quinolin-4-yloxy]-cyclopentanecarbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester → 17-[2-(4-Isopropyl-thiazol-2-yl)-7-methoxy-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl ester

HRID 1516668
ノート
印刷プレビュー

反応式

HRID 1516668 の反応式
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[S:33][CH:34]=[C:35]([CH:37]([CH3:39])[CH3:38])[N:36]=4)[CH:21]=3)[CH2:16][CH:15]2[C:40](=[O:49])[N:41]([CH2:43][CH2:44][CH2:45][CH2:46][CH:47]=C)[CH3:42])=[O:13])[CH2:8][CH:7]1[CH:9]=C)=[O:5])[CH3:2]>ClCCCl>[CH2:1]([O:3][C:4]([C:6]12[CH2:8][CH:7]1[CH:9]=[CH:47][CH2:46][CH2:45][CH2:44][CH2:43][N:41]([CH3:42])[C:40](=[O:49])[CH:15]1[CH:14]([CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[S:33][CH:34]=[C:35]([CH:37]([CH3:39])[CH3:38])[N:36]=4)[CH:21]=3)[CH2:16]1)[C:12](=[O:13])[NH:11]2)=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

3

反応物 1

HCID 674117151-({2-(Hex-5-enyl-methyl-carbamoyl)-4-[2-(4-isopropyl-thiazol-2-yl)-7-methoxy-quinolin-4-yloxy]-cyclopentanecarbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester

生成物 1

HCID 6741035617-[2-(4-Isopropyl-thiazol-2-yl)-7-methoxy-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl ester収率 73.3%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

1-({2-(Hex-5-enyl-methyl-carbamoyl)-4-[2-(4-isopropyl-thiazol-2-yl)-7-methoxy-quinolin-4-yloxy]-cyclopentanecarbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester (33, 280 mg) was dissolved in DCE (280 mL) in a reflux setup. The system was successively evacuated and filled with argon (repeated 3 times). Then, Hoveyda-Grubbs 2nd generation catalyst (28 mg) was added and the system was evacuated and filled with argon twice. The resulting mixture was successively heated to refluxed overnight, concentrated, and subjected to flash column chromatography (silica, AcOEt/hexane) to give 197 mg (73%) of the title product 34 as grey-brown solid: m/z=661 (M+H)+.

後処理

  1. customThe system was successively evacuated
  2. additionfilled with argon (repeated 3 times)
  3. additionThen, Hoveyda-Grubbs 2nd generation catalyst (28 mg) was added
  4. customthe system was evacuated
  5. additionfilled with argon twice
  6. temperatureThe resulting mixture was successively heated
  7. temperatureto refluxed overnight
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-c0a28ce0e5894625aa229670ecb16c01
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08227407B2

反応ノート

読み込み中…

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