Hydrochloric Acid → ({2-Chloro-5-[5-(3-chlorothiophene-2-yl)-(1,2,4]oxadiazol-3-yl]-phenyl}-methylamino)-acetic acid

HRID 856983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 856983
C([O:3][C:4](=[O:26])[CH2:5][N:6]([C:8]1[CH:13]=[C:12]([C:14]2[N:18]=[C:17]([C:19]3[S:20][CH:21]=[CH:22][C:23]=3[Cl:24])[O:16][N:15]=2)[CH:11]=[CH:10][C:9]=1[Cl:25])[CH3:7])C.[OH-].[Na+].Cl>C1COCC1.C(O)C.O>[Cl:25][C:9]1[CH:10]=[CH:11][C:12]([C:14]2[N:18]=[C:17]([C:19]3[S:20][CH:21]=[CH:22][C:23]=3[Cl:24])[O:16][N:15]=2)=[CH:13][C:8]=1[N:6]([CH2:5][C:4]([OH:26])=[O:3])[CH3:7]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 16222813((2-Chloro-5-[5-(3-chlorothiophene-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-methylamino)-acetic acid ethyl ester

Produkt 1

HCID 16222814({2-Chloro-5-[5-(3-chlorothiophene-2-yl)-(1,2,4]oxadiazol-3-yl]-phenyl}-methylamino)-acetic acidAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a white suspension of ({2-chloro-5-[5-(3-chlorothiophene-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-methylamino)-acetic acid ethyl ester (0.362 g, 0.880 mmol) in an EtOH:H2O solution (4:1, 13.4 mL) was added 1M NaOH (0.033 mL, 0.84 mmol). Additional aliquots of 1M NaOH (1.98 μL, 50.34 mmol), ethanol (8 mL) and THF (10 mL) was added and the mixture was stirred for 2 days until the reaction was complete by TLC. The reaction suspension was neutralized by the addition of 1M HCl and concentrated to a white solid. The white solid was filtered and washed with H2O and ether to yield 0.142 g (44%) of the title compound as a yellow solid. 1H NMR (DMSO-d6): 8.19 (dd, 1H, J=5.2 and 0.8 Hz), 7.79 (s, 1H), 7.52 (dd, 2H, J=8.2 and 6.3 Hz), 7.41 (dd, 1H, J=5.5 Hz), 3.77 (s, 2H), 2.97 (s, 3H).

Aufarbeitung

  1. concentrationconcentrated to a white solid
  2. filtrationThe white solid was filtered
  3. washwashed with H2O and ether

Quellen und Nachweise

ORD-Eintrag
ord-af59ecf45899413a9c29b922e471c0f3
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144876B2

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