Benzathine → (RS)-4-{4-[3-(4-chloro-phenyl)-ureido]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1805213

Reaktionsgleichung

Reaktionsgleichung von HRID 1805213
[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=2)[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH2:32])=[O:31])=[CH:25][CH:24]=1.[F-].[K+].C(NCCNCC1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([NH:32][C:30]([NH:29][C:26]3[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=3)=[O:31])=[CH:15][CH:14]=2)[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 8793BenzathineHCID 87964-ChlorophenylureaHCID 522689Potassium FluorideHCID 67151644(RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Produkt 1

HCID 67151498(RS)-4-{4-[3-(4-chloro-phenyl)-ureido]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl esterAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A stirred suspension of (RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.60 g), 4-chlorophenylurea (0.81 g), potassium fluoride (2.88 g, 40 wt % on alumina), N,N′-dibenzylethylenediamine (0.14 ml) and copper(I) iodide (0.11 g) in THF (16 ml) in a sealed tube was heated at 90° C. for 30 minutes under microwave irradiation. The mixture was then cooled to room temperature and filtered through celite. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (RS)-4-{4-[3-(4-chloro-phenyl)-ureido]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.24 g, 14%) as a light yellow solid. MS (ISP): 392.1 ([{37Cl}M+H—C4H8]+), 390.1 ([{35Cl}M+H—C4H8]+).

Aufarbeitung

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-07b2e2e9e8924e7a82757d4df75d472a
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354441B2

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