Sodium Hydroxide → [1-(2-Chloro-4-ethanesulfonyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid

HRID 1445610

Reaktionsgleichung

Reaktionsgleichung von HRID 1445610
C[O:2][C:3](=[O:28])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH2:24][CH3:25])(=[O:23])=[O:22])=[CH:17][C:16]=2[Cl:26])[C:6]=1[CH3:27].[OH-].[Na+]>CO.C1COCC1>[Cl:26][C:16]1[CH:17]=[C:18]([S:21]([CH2:24][CH3:25])(=[O:22])=[O:23])[CH:19]=[CH:20][C:15]=1[CH2:14][N:7]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:13]2[C:5]([CH2:4][C:3]([OH:28])=[O:2])=[C:6]1[CH3:27]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67219537[1-(2-Chloro-4-ethanesulfonyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester

Produkt 1

HCID 11704178[1-(2-Chloro-4-ethanesulfonyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of [1-(2-chloro-4-ethanesulfonyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester: (3.32 g, 7.89 mmol) in methanol/THF (30 ml of a 1:1 mixture) is added 1M NaOH (15 ml). After stirring at room temperature overnight, the solvent is removed in vacuo and the residue is dissolved in water (20 ml). The solution is acidified to pH1 using 6M HCl and the resulting suspension is filtered and recrystallised from IPA/water to yield the titled product. (MH+ 407)

Aufarbeitung

  1. customthe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in water (20 ml)
  3. filtrationthe resulting suspension is filtered
  4. customrecrystallised from IPA/water

Quellen und Nachweise

ORD-Eintrag
ord-46e0ee431ed5414791c0b284f63d6704
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666878B2

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