Hydrochloric Acid → octanedioic acid [4-(3-Nitro-phenyl)-thiazol-2-yl]-amide

HRID 243624

Reaktionsgleichung

Reaktionsgleichung von HRID 243624
C[O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=2)[N:17]=1)=[O:11].O[Li].O.Cl>CO.O>[N+:24]([C:20]1[CH:19]=[C:18]([C:16]2[N:17]=[C:13]([NH:12][C:10](=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:27])=[O:2])[S:14][CH:15]=2)[CH:23]=[CH:22][CH:21]=1)([O-:26])=[O:25]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 44550802octanedioic acid [4-(3-Nitro-phenyl)-thiazol-2-yl]-amide methyl ester

Produkt 1

HCID 16733292octanedioic acid [4-(3-Nitro-phenyl)-thiazol-2-yl]-amideAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of compound 14 (0.391 g, 1.0 mmol) in a mixture of MeOH (10 ml) and water (10 ml) was added LiOH—H2O (0.839 g, 20.0 mmol), and the mixture was stirred at room temperature for 3 hour. Then the reaction mixture was acidified with 1N HCl dropwise to pH 5 and extracted with EtOAc. The organic layer was washed with water and saturated brine and dried over Na2SO4. The solvent was evaporated to give compound 18 (0.322 g, 85.6%). 1H NMR (300 MHz, DMSO-d6) δ12.3 (1H, s), 8.72 (1H, s), 8.33 (1H, d, J=7.6 Hz), 8.16 (1H, dd, J=7.9, 2.8 Hz), 7.91 (1H, s), 7.72 (1H, t, J=8.0 Hz), 2.45 (2H, t, J=6.5 Hz), 2.19 (2H, t, J=5.7 Hz), 1.60 (2H, brs), 1.49 (2H, t, J=6.3 Hz), 1.30-1.18 (4H, m). 13C NMR (75 MHz, DMSO-d6) M75.3, 172.5, 159.2, 149.1, 147.1, 136.6, 132.5, 131.2, 123.0, 120.9, 111.2, 35.7, 34.4, 31.2, 29.1, 25.3, 25.1.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-dcd20dc49b1a4bfbb291063c427c12f2
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653278B2

Verknüpfte Notizen

Wird geladen…