Potassium Carbonate → HCID 68586517, Verbindung

HRID 2189500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2189500
Cl[CH2:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([OH:29])=[C:23]([NH:25][C:26]([NH2:28])=[O:27])[CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:29][CH2:2][C:3]([CH:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)=[O:4])=[C:23]([NH:25][C:26]([NH2:28])=[O:27])[CH:24]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 11435385(5-Chloro-2-hydroxy-phenyl)-ureaHCID 24229336Tert-butyl 4-(2-chloroacetyl)piperidine-1-carboxylate2×

Produkt 1

HCID 68586517HCID 68586517, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of the crude tert-butyl 4-(2-chloroacetyl)piperidine-1-carboxylate (one third the material from step 1, approximately 5 mmol) in DMSO (20 mL) was charged with 1-(5-chloro-2-hydroxyphenyl)urea (see N. Hossain et al., WO PCT 2004/005295; 980 mg, 5.25 mmol) and K2CO3 (1.38 g, 10 mmol). The reaction was stirred for ˜14 h and then quenched with water (40 mL). The mixture was extracted twice with EtOAc. The organic phases were combined, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resultant residue was purified by flash chromatography to afford tert-butyl 4-(2-(4-chloro-2-ureidophenoxy)acetyl)piperidine-1-carboxylate (550 mg, ˜25% yield) as a solid. LC/MS [M-Boc]+=312.3, [M+Na]+=434.3.

Aufarbeitung

  1. customquenched with water (40 mL)
  2. extractionThe mixture was extracted twice with EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0b3918c320854fa59890dd0f04ec97ed
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324251B2

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