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

HRID 882255Notes

Reaction equation

HRID 882255 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([O:22]C)=[O:21])=[N:18][CH:19]=3)=[CH:11][CH:12]=2)[C@H:7]([NH2:24])[CH2:6][C@@H:5]1[CH3:25])(=[O:3])[CH3:2].O.[OH-].[Li+]>CO.O>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([OH:22])=[O:21])=[N:18][CH:19]=3)=[CH:11][CH:12]=2)[C@H:7]([NH2:24])[CH2:6][C@@H:5]1[CH3:25])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86709423HCID 86709423, compound

Product 1

HCID 867094245-((2S,4R)-1-acetyl-4-amino-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinic acidYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To methyl 5-((2S,4R)-1-acetyl-4-amino-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinate (for a preparation, see Intermediate 54) (550 mg, 1.62 mmol) in MeOH (5 mL) was added lithium hydroxide monohydrate (78 mg, 3.24 mmol) in water (5 mL) and the mixture stirred at room temperature for 90 mins. The mixture was concentrated in vacuo before DCM was added. The mixture was filtered, dried by passing through a hydrophobic frit, and concentrated in vacuo to give 5-((2S,4R)-1-acetyl-4-amino-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinic acid (517 mg, 1.59 mmol, 98% yield).

Workup

  1. concentrationThe mixture was concentrated in vacuo before DCM
  2. additionwas added
  3. filtrationThe mixture was filtered
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a29f7fae31764f35b84225bb41e7d447
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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