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

HRID 882255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882255
[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]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 86709423HCID 86709423, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a29f7fae31764f35b84225bb41e7d447
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993554B2

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