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 882260Notes

Reaction equation

HRID 882260 reaction equation
[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]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 70976543ethyl 4-((2S,4R)-1-acetyl-2-methyl-4-((5-methylpyridin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-95561993c41849ea827bd91395884ab1
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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