Chlorosuccinimide → tert-Butyl 4-{4-[5-(2-chloro-6-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

HRID 38738

Reaktionsgleichung

Reaktionsgleichung von HRID 38738
[OH:1][N:2]=[CH:3][C:4]1[N:5]=[C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[S:7][CH:8]=1.ClN1C(=O)CCC1=O.[Cl:30][C:31]1[C:32]([CH:38]=[CH2:39])=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=1.C(=O)([O-])O.[K+]>C(OCC)(=O)C.O>[Cl:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[C:32]=1[CH:38]1[O:1][N:2]=[C:3]([C:4]2[N:5]=[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]3)[S:7][CH:8]=2)[CH2:39]1

Komponenten

8

Edukt 4

HCID 31398ChlorosuccinimideHCID 516893Potassium BicarbonateHCID 189709553-Chloro-2-vinylphenolHCID 86657567Tert-butyl 4-(4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl)piperidine-1-carboxylate

Produkt 1

HCID 67244553tert-Butyl 4-{4-[5-(2-chloro-6-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of tert-butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (400 mg) in ethyl acetate (10 ml) was added N-chlorosuccinimide (206 mg). The reaction mixture is stirred at reflux for 30 min. To the reaction mixture were added 3-chloro-2-vinylphenol (397 mg) and potassium hydrogencarbonate (257 mg) at room temperature, and then one drop of water. After stirring at room temperature overnight, the reaction mixture was admixed with ethyl acetate and water and extracted with ethyl acetate. The organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave tert-butyl 4-{4-[5-(2-chloro-6-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (345 mg).

Aufarbeitung

  1. temperatureat reflux for 30 min
  2. stirringAfter stirring at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ac0a7783ad7e4fc3967ed391fe24bd19
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524743B2

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