Glycine → HCID 24757067, Verbindung

HRID 642284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642284
C(O[C:4]([C:6]1[N:11]=[C:10]([CH3:12])[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:22])=[O:5])C.[NH2:23][CH2:24][C:25]([OH:27])=[O:26]>C[O-].[Na+].CO>[OH:22][C:7]1[C:8]2[S:15][C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:13][C:9]=2[C:10]([CH3:12])=[N:11][C:6]=1[C:4]([NH:23][CH2:24][C:25]([OH:27])=[O:26])=[O:5]

Komponenten

4

Edukt 2

HCID 750GlycineHCID 68426288HCID 68426288, Verbindung

Produkt 1

HCID 24757067HCID 24757067, VerbindungAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23694274Sodium methanolate methanolLösungsmittel

Versuchsvorschrift

A mixture of 7-hydroxy-4-methyl-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (159 mg, 0.51 mmol) and glycine (760 mg, 1.01 mmol) in 0.5 M sodium methoxide/methanol (19.2 mL) was refluxed for three days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (50 mL) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (12 mL). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (127 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.01 (br s, 1H), 9.24 (br s, 1H), 8.14 (m, 2H), 7.62 (m, 3H), 4.03 (d, J=6.2 Hz, 2H), 2.87 (s, 3H); MS: (+) m/z 344.0 (M+1)

Aufarbeitung

  1. temperaturewas refluxed for three days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (50 mL)
  4. extractionextracted twice with dichloromethane
  5. filtrationThe solid precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b6f439e8868e4274997e063fde0b159f
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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