Water → lithium 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

HRID 882258Notes

Reaction equation

HRID 882258 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][CH:29]=[CH:28][N:27]=2)[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2].O.O.[OH-].[Li+:36]>CCO>[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][CH:29]=[CH:28][N:27]=2)[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2].[Li+:36]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrate2×HCID 86709426ethyl 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

Product 1

HCID 70976493lithium 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (for a preparation see Intermediate 57) (216 mg, 0.503 mmol) in EtOH (1 mL) and water (0.5 mL) was treated with lithium hydroxide monohydrate (22 mg, 0.524 mmol) and the mixture stirred at r.t. over the weekend. A further portion of lithium hydroxide monohydrate (4 mg, 0.095 mmol) was added to the reaction and the mixture stirred for 1 h. The mixture was concentrated to dryness to give the crude product lithium 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (160 mg) which was used directly in the next step without further purification.

Workup

  1. stirringthe mixture stirred for 1 h
  2. concentrationThe mixture was concentrated to dryness

Sources & evidence

ORD record
ord-131f290312714c2ab0187b5a7a93de60
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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