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

HRID 642317Notizen

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of 7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester (31 mg, 0.10 mmol) and glycine (78 mg, 1.04 mmol) in 0.5 M sodium methoxide/methanol (1.7 mL) was heated at 120° C. using a CEM microwave reactor for 30 min before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (18 mL) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (1.2 mL). The resulting precipitate was filtered, washed with water and dried in vacuo to give the title compound as a yellow solid (25 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.30 (br s, 1H), 9.42 (t, 1H), 8.96 (s, 1H), 8.14 (m, 2H), 7.67 (m, 3H), 4.02 (d, J=6.2 Hz, 2H); MS: (+) m/z 330.0 (M+1).

Aufarbeitung

customfor 30 min
temperaturewas cooled to room temperature
concentrationconcentrated in vacuo
dissolutionThe residue was dissolved in water (18 mL)
extractionextracted twice with dichloromethane
filtrationThe resulting precipitate was filtered
washwashed with water
customdried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-ad8ca9e41fd047c5bb36afebf9557fcb
Quelldatensatz: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07696223B2

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