Glycine → [(7-Hydroxy-2,4-diphenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid

HRID 642282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642282
C(O[C:4]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[N:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[S:20][C:8]=2[C:7]=1[OH:27])=[O:5])C.[NH2:28][CH2:29][C:30]([OH:32])=[O:31]>C[O-].[Na+].CO>[OH:27][C:7]1[C:8]2[S:20][C:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[N:18][C:9]=2[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:11][C:6]=1[C:4]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:5]

Komponenten

4

Edukt 2

HCID 750GlycineHCID 684280397-Hydroxy-2,4-diphenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Produkt 1

HCID 24757066[(7-Hydroxy-2,4-diphenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acidAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23694274Sodium methanolate methanolLösungsmittel

Versuchsvorschrift

A mixture of 7-hydroxy-2,4-diphenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (45 mg, 0.12 mmol) and glycine (179 mg, 2.38 mmol) in 0.5 M sodium methoxide/methanol (4.5 mL) was refluxed for four days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (20 mL) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (3 mL). The suspension was extracted with ethyl acetate (2×25 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (47 mg): 1H NMR (DMSO-d6, 200 MHz): δ=9.46 (t, 1H), 8.68 (m, 2H), 8.22 (m, 2H), 7.65 (m, 6H), 4.09 (m, 2H); MS: (+) m/z 406.0 (M+1)

Aufarbeitung

  1. temperaturewas refluxed for four days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (20 mL)
  4. extractionextracted twice with dichloromethane
  5. extractionThe suspension was extracted with ethyl acetate (2×25 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5c4cd24530834db2928ddf469d5144d9
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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