Water → HCID 58055087, Verbindung

HRID 1685005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685005
CON.[F:4][C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][CH:25]=1)[CH2:8][NH:9][C:10](=[O:22])[NH:11][C:12]1[S:13][CH:14]=[C:15]([CH2:17][N:18](OC)[CH3:19])[N:16]=1.O>CC(O)=O.[Zn]>[F:4][C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][CH:25]=1)[CH2:8][NH:9][C:10]([NH:11][C:12]1[S:13][CH:14]=[C:15]([CH2:17][NH:18][CH3:19])[N:16]=1)=[O:22]

Komponenten

6

Edukt 3

HCID 962WaterHCID 4113O-MethylhydroxylamineHCID 58055072HCID 58055072, Verbindung

Produkt 1

HCID 58055087HCID 58055087, VerbindungAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator2×HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Zinc Reduction of methoxyamine to amine (J. Natural Products 53(4), 995-999 (1990)). A solution of 2-(3-(3-fluorobenzyl)ureido)-4-(N-methoxy-N-methyl-aminomethyl)-thiazole (10.1 g, 31.1 mmol) in glacial HOAc (140 mL) was treated with micronized zinc dust (50 g) and the mixture was heated to 60-65 C with vigorous agitation. The reduction was complete in 2-16 hours and water (140 mL) was added. The mixture was filtered on Celite, the filter cake was reslurried in 1:1 HOAC:water (150 mL) and refiltered. The combine filtrate was made alkaline to pH 10 with NH4OH and cooled in ice. The solids were collected by filtration, washed with water, and dried in vacuo to afford Intermediate 5 as an off-white solid (8.2 g, 89% yield). This product could be used directly or further purified by crystallization as the hydrochloride salt (1:1 MeOH:EtOH).

Aufarbeitung

  1. temperaturethe mixture was heated to 60-65 C with vigorous agitation
  2. filtrationThe mixture was filtered on Celite
  3. temperaturecooled in ice
  4. filtrationThe solids were collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a75254847e8f421f898e6fb9d4335cb1
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148380B2

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