Water → HCID 71238166, Verbindung

HRID 1846659Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846659
C([O:3][C:4](=[O:30])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([NH:18][C:19](=[O:27])[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)=[CH:16][C:15]([C:28]#[N:29])=[CH:14][N:13]=2)[CH2:8][CH2:7]1)C.O.[OH-].[Li+]>C1COCC1.CO>[Cl:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[C:19]([NH:18][C:17]1[C:12]([N:9]2[CH2:8][CH2:7][CH:6]([CH2:5][C:4]([OH:30])=[O:3])[CH2:11][CH2:10]2)=[N:13][CH:14]=[C:15]([C:28]#[N:29])[CH:16]=1)=[O:27]

Komponenten

6

Edukt 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 71238641HCID 71238641, Verbindung

Produkt 1

HCID 71238166HCID 71238166, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 0.047 g (0.11 mmol) of [3′-(3-chloro-benzoylamino)-5′-cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester in a mixture of THF (5 mL) and MeOH (2 mL) is added water (1 mL) and 0.013 g (0.55 mmol) of lithium hydroxide. The reaction mixture is stirred at room temperature for three days. The solvent is removed under reduced pressure and the residue is taken back up into water. The pH of the resulting aqueous solution is adjusted to approximately pH2 by adding concentrated hydrochloric acid which results in a solid precipitating from solution. The formed precipitate is collected by filtration, washed with water, and dried under vacuum to give 0.035 g (80%) of [3′-(3-chloro-benzoylamino)-5′-cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid as yellow solid.

Aufarbeitung

  1. customThe solvent is removed under reduced pressure
  2. additionby adding concentrated hydrochloric acid which
  3. customresults in a solid
  4. customprecipitating from solution
  5. filtrationThe formed precipitate is collected by filtration
  6. washwashed with water
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-049a5036e8364081aeb2d67c41bbe84c
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952004B2

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