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Water → HCID 59410204, Verbindung

HRID 85234
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 85234
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@@H:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[C:21]([CH3:23])[C:20]([N:24]4[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[C:25]4=[O:31])=[C:19]([CH3:32])[CH:18]=3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1.Br[CH2:34][CH2:35][Cl:36].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN1CCCC1=O>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@@H:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[C:21]([CH3:23])[C:20]([N:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:34][CH2:35][Cl:36])[C:25]4=[O:31])=[C:19]([CH3:32])[CH:18]=3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 10796Cesium carbonateHCID 594101745-Chloro-N-({(5S)-3-[4-(3-hydroxy-2-oxopyridin-1(2H)-yl)-3,5-dimethylphenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide

Produkt 1

HCID 59410204HCID 59410204, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

900 mg (1.89 mmol) of the compound from Example 72A and 1.36 g (9.49 mmol) of 1-bromo-2-chloroethane are dissolved in 30 ml of 1-methyl-2-pyrrolidone. 1.55 g (4.75 mmol) of caesium carbonate are added to the solution, and the mixture is stirred at 60° C. for 15 hours. Water is then added, and, after phase separation, the aqueous phase is extracted three times with tert-butyl methyl ether and three times with dichloromethane. The combined organic phases are washed successively with 1N aqueous sodium hydroxide solution and saturated sodium chloride solution and then dried over sodium sulphate. The drying agent is filtered off and the solvent is removed completely on a rotary evaporator. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:5). This gives 464 mg (45% of theory, purity according to LC-MS 74%) of the desired product.

Aufarbeitung

  1. customafter phase separation
  2. extractionthe aqueous phase is extracted three times with tert-butyl methyl ether and three times with dichloromethane
  3. washThe combined organic phases are washed successively with 1N aqueous sodium hydroxide solution and saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. filtrationThe drying agent is filtered off
  6. customthe solvent is removed completely on a rotary evaporator
  7. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:5)

Quellen und Nachweise

ORD-Eintrag
ord-0a8d2d20ede645d0a2b087d79cb89fd2
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846934B2

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