Triethylamine → 5-Chloro-N-{[(5S)-3-(3-isopropyl-2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}-2-thiophenecarboxamide

HRID 68469

Reaktionsgleichung

Reaktionsgleichung von HRID 68469
Cl.[NH2:2][CH2:3][C@@H:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:22]=[CH:21][C:13]3[N:14]([CH:18]([CH3:20])[CH3:19])[C:15](=[O:17])[O:16][C:12]=3[CH:11]=2)[CH2:5]1.C(N(CC)CC)C.[Cl:30][C:31]1[S:35][C:34]([C:36](Cl)=[O:37])=[CH:33][CH:32]=1>O1CCCC1>[Cl:30][C:31]1[S:35][C:34]([C:36]([NH:2][CH2:3][C@@H:4]2[O:8][C:7](=[O:9])[N:6]([C:10]3[CH:22]=[CH:21][C:13]4[N:14]([CH:18]([CH3:20])[CH3:19])[C:15](=[O:17])[O:16][C:12]=4[CH:11]=3)[CH2:5]2)=[O:37])=[CH:33][CH:32]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 5892235-Chlorothiophene-2-carbonyl ChlorideHCID 574966626-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]-3-isopropyl-1,3-benzoxazol-2(3H)-one hydrochloride

Produkt 1

HCID 574966615-Chloro-N-{[(5S)-3-(3-isopropyl-2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}-2-thiophenecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

200 mg (0.61 mmol) of 6-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]-3-isopropyl-1,3-benzoxazol-2(3H)-one hydrochloride (EP 738726) are suspended in 5 ml of tetrahydrofuran and admixed with 0.26 ml (1.83 mmol) of triethylamine and 132 mg (0.73 mmol) of 5-chlorothiophene-2-carbonyl chloride. The reaction mixture is stirred at room temperature overnight and then concentrated. The product is isolated by column chromatography (silica gel, methylene chloride/ethanol=50/1 to 20/1). This gives 115 mg (43% of theory) of the desired compound.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe product is isolated by column chromatography (silica gel, methylene chloride/ethanol=50/1 to 20/1)

Quellen und Nachweise

ORD-Eintrag
ord-40ac4258f5644bfdaf57abffed19acfc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822458B2

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