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Potassium Hydroxide → 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoic acid

HRID 1786049
ノート
印刷プレビュー

反応式

HRID 1786049 の反応式
[C:1]([N:4]([C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:35]=[CH:34][C:20]([O:21][CH2:22][CH2:23][CH:24]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[C:25]([O:27]C)=[O:26])=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:36])[CH2:6]1)(=[O:3])[CH3:2].[OH-].[K+]>O1CCCC1.CO>[C:1]([N:4]([C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:35]=[CH:34][C:20]([O:21][CH2:22][CH2:23][CH:24]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[C:25]([OH:27])=[O:26])=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:36])[CH2:6]1)(=[O:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 68920582methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro-quinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoate

生成物 1

HCID 575955164-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoic acid収率 55%

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran
溶媒

反応条件

温度
50 °C

実験手順

Methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro-quinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoate was hydrolyzed to the acid by dissolving in 6 ml tetrahydrofuran/methanol (1/1) and potassium hydroxide (0.04 g in 2 ml water) was added. The mixture was heated to 50° C. for 18 hours. The mixture was cooled to room temperature and concentrated. Then neutralized with 1M HCl and extracted with dichloromethane. The dichloromethane solution was dried and concentrated. The residue was purified by silica gel chromatography (87% CH2Cl2/13% methanol) to afford 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoic acid (0.04 g, 55%).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. extractionextracted with dichloromethane
  4. dry with materialThe dichloromethane solution was dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (87% CH2Cl2/13% methanol)

出典と根拠

ORDレコード
ord-41a7afebb8de40dc819fe91dbbc286c1
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07504508B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート