Lithium hydroxide, monohydrate → lithium 4-((2S,4R)-1-acetyl-2-methyl-4-((5-methylpyridin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

HRID 882260노트

반응식

HRID 882260 반응식
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][N:27]=2)[CH2:6][C@@H:5]1[CH3:33])(=[O:3])[CH3:2].O.[OH-].[Li+:36]>CCO.O>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:24]=[CH:23][C:17]([C:18]([O-:20])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][N:27]=2)[CH2:6][C@@H:5]1[CH3:33])(=[O:3])[CH3:2].[Li+:36]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrate2회HCID 70976543ethyl 4-((2S,4R)-1-acetyl-2-methyl-4-((5-methylpyridin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate2회

생성물 1

HCID 86709427lithium 4-((2S,4R)-1-acetyl-2-methyl-4-((5-methylpyridin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate수율 106.1%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

Crude ethyl 4-((2S,4R)-1-acetyl-2-methyl-4-((5-methylpyridin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (Intermediate 59) (238 mg) in EtOH (2 mL) and water (1 mL) was treated with lithium hydroxide monohydrate (26 mg, 0.620 mmol). The solution was stirred at ambient temperature for 5 h. A further portion of lithium hydroxide monohydrate (4 mg, 0.095 mmol) was added and the mixture left at ambient temperature overnight. The mixture was concentrated to dryness to give crude lithium 4-((2S,4R)-1-acetyl-2-methyl-4-((5-methylpyridin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate as a brown foam (240 mg) which was used directly in the next step without further purification. LCMS: (Formate, 2 min), Rt=0.65 min, MH+416.

후처리

  1. waitthe mixture left at ambient temperature overnight
  2. concentrationThe mixture was concentrated to dryness

출처 및 근거

ORD 기록
ord-95561993c41849ea827bd91395884ab1
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993554B2

반응 노트

불러오는 중…