Dimethylformamide → 4-[(5S)-5-[(ethanethioylamino)methyl]-2-oxo-oxazolidin-3-yl]-2-fluoro-benzamide

HRID 351873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351873
[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([NH2:17])=[O:16])=[C:11]([F:18])[CH:10]=2)[CH2:4]1.C(N(CC)CC)C.[C:26](SCC)(=[S:28])[CH3:27].CN(C=O)C>C(#N)C>[C:26]([NH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([NH2:17])=[O:16])=[C:11]([F:18])[CH:10]=2)[CH2:4]1)(=[S:28])[CH3:27]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 70093Ethyl dithioacetateHCID 229661984-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-benzamide

Produkt 1

HCID 30064334-[(5S)-5-[(ethanethioylamino)methyl]-2-oxo-oxazolidin-3-yl]-2-fluoro-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 5-(S)-aminomethyl-3-[4′-aminocarbonyl-3′-fluorophenyl]oxazolidine-2-one (1.75 g, 6.9 mmol), triethylamine (2.0 ml, 13.8 mmol) and ethyl dithioacetate (0.87 ml, 7.6 mmol) and DMF (5 ml) in acetonitrile (5 ml) was stirred at r.t. for 48 h. Solvent was removed under vacuum, and the crude material purified by silica gel chromatography (eluent: 10% methanol in ethyl acetate). White crystalline solid (1.3 g, 61%). HPLC Rt=4.5 min. MS (m/z): [M+H]+=312.

Aufarbeitung

  1. customSolvent was removed under vacuum
  2. customthe crude material purified by silica gel chromatography (eluent: 10% methanol in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-316b602e5ef6489ab036878ce210de8d
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743811B2

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