Sodium Hydroxide → 2-(4-(Cyclobutanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 1801353ノート

反応式

HRID 1801353 の反応式
[CH:1]1([C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[C:23]([CH3:25])([CH3:24])[CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:26]([O:28]C)=[O:27])[CH:20]=4)[NH:15]3)=[CH:10][CH:9]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO.O>[CH:1]1([C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[C:23]([CH3:25])([CH3:24])[CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:26]([OH:28])=[O:27])[CH:20]=4)[NH:15]3)=[CH:10][CH:9]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 67439894Methyl 2-(4-(cyclobutanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

生成物 1

HCID 584761422-(4-(Cyclobutanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid収率 84%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒2 回

実験手順

To a mixture of methyl 2-(4-(cyclobutanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (42 mg, 0.21 mmol) in methanol (3 mL) and water (1.5 mL) was treated with a solution of sodium hydroxide (133 mg, 2.63 mmol) in water (1.5 mL). The resultant mixture was heated to reflux until the completion of the reaction (monitored by thin layer chromatography). The methanol was removed under vacuum. The residue was acidified with 2M hydrochloric acid to pH=1. The precipitates were collected by filtration to afford 30 mg of 2-(4-(cyclobutanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a yellow solid Yield: 84%. MS (ESI+APCI) M+1=379.2.

後処理

  1. temperatureto reflux until the completion of the reaction (monitored by thin layer chromatography)
  2. customThe methanol was removed under vacuum
  3. filtrationThe precipitates were collected by filtration

出典と根拠

ORDレコード
ord-f5b489742956487290c0bb3017122279
出典データセット
uspto-grants-2013_01
特許番号
US08344137B2

反応ノート

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