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

HRID 1801353노트

반응식

HRID 1801353 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f5b489742956487290c0bb3017122279
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344137B2

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