Triethylamine → N-((5S)-3-(4-(1-Methylsulfonyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)-2-oxo-oxazolidin-5-ylmethyl)acetamide

HRID 650275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 650275
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[NH:13]1[CH2:18][CH2:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]3=[O:35])=[CH:21][CH:20]=2)=[CH:15][CH2:14]1>ClCCl>[CH3:8][S:9]([N:13]1[CH2:18][CH2:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]3=[O:35])=[CH:21][CH:20]=2)=[CH:15][CH2:14]1)(=[O:11])=[O:10]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20638827N-((5S)-3-(4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide

Produkt 1

HCID 57166224N-((5S)-3-(4-(1-Methylsulfonyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)-2-oxo-oxazolidin-5-ylmethyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Triethylamine (253 mg), followed by a solution of methanesulfonyl chloride (69 mg) in dichloromethane (1 ml) was added, with ice-bath cooling, to a stirred suspension of N-((5S)-3-(4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide (215 mg, Example 2) in dichloromethane (10 ml). TLC showed complete reaction after 2 hours. The reaction mixture was washed with 2N. HCl, water, saturated sodium hydrogen carbonate and brine. The organic phase was dried over anhydrous sodium sulfate and evaporated to give the title compound as a crystalline solid which was recrystallised from acetonitrile (yield=117 mg, 60%).

Aufarbeitung

  1. additionwas added, with ice-bath
  2. customreaction after 2 hours
  3. washThe reaction mixture was washed with 2N
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-75d4d543703645f08ca6288db324cff5
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271383B1

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