Hydrochloric Acid → N1-(4-(3-aminophenyl)thiazol-2-yl)-N8-hydroxyoctanediamide

HRID 243627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 243627
Cl.[NH2:2][OH:3].CO.[OH-].[K+].C[O:9][C:10](=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:19][C:20]1[S:21][CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[CH:26]=2)[N:24]=1)=[O:18].[OH-].[K+].Cl>O>[NH2:31][C:27]1[CH:26]=[C:25]([C:23]2[N:24]=[C:20]([NH:19][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]([NH:2][OH:3])=[O:9])[S:21][CH:22]=2)[CH:30]=[CH:29][CH:28]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 23689386Potassium hydroxide methanolHCID 44550930octanedioic acid [4-(3-Amino-phenyl)-thiazol-2-yl]-amide methyl ester

Produkt 1

HCID 24178404N1-(4-(3-aminophenyl)thiazol-2-yl)-N8-hydroxyoctanediamideAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of hydroxylamine hydrochloride (0.958 g, 13.8 mmol) in MeOH-KOH (0.772 g, 13.8 mmol) was added at 40° C. for 10 minutes. The reaction mixture was cooled to 0° C. and filtered. Compound 20 (0.250 g, 0.69 mmol) was added to the filtrate followed by KOH (50 mg, 0.89 mmol) at room temperature. After 2 hours, water (20 ml) was added, followed by 1 N HCl until pH reached 6.5. The reaction mixture was extracted with EtOAc, and organic layer was washed with brine, dried over Na2SO4 and filtered. The solvent was removed by rotary evaporation. The crude solid was purified by preparative HPLC to give compound 23 (0.110 g, 43.9%). 1H NMR (300 MHz, CD3OD) δ 7.98 (1H, d, J=7.8 Hz), 7.90 (1H, s), 7.55 (1H, t, J=7.8 Hz), 7.51 (1H, s), 7.29 (1H, dd, J=7.8, 1.2 Hz), 2.51 (2H, t, J=7.2 Hz), 2.11 (2H, t, J=7.2 Hz), 1.74 (2H, t, J=7.0 Hz), 1.65 (2H, t, J=7.0 Hz), 1.50-1.35 (4H, m). 13C NMR (100 MHz, CD3OD) δ 172.1, 158.0, 147.4, 136.3, 129.7, 125.1, 120.8, 119.2, 108.5, 34.6, 28.0, 27.9, 24.7, 24.3.

Aufarbeitung

  1. filtrationfiltered
  2. extractionThe reaction mixture was extracted with EtOAc, and organic layer
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed by rotary evaporation
  7. customThe crude solid was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0537ac75dd924afb9ff738e965e9a7c6
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653278B2

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