Triethylamine → HCID 86757454, Verbindung

HRID 1597705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1597705
Br[CH2:2][C:3]([NH:5][C@@H:6]1[C:13](=[O:14])[N:12]2[C@@H:7]1[S:8][CH2:9][C:10](/[CH:18]=[C:19]1/[C:20](=[O:43])[N:21]([CH2:24][C:25]3[CH:30]=[CH:29][N+:28]([CH2:31][C:32](=[O:42])[NH:33][C:34]4[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([F:41])[CH:35]=4)=[CH:27][CH:26]=3)[CH2:22][CH2:23]/1)=[C:11]2[C:15]([O-:17])=[O:16])=[O:4].[CH3:44][N:45]1[CH:49]=[N:48][N:47]=[C:46]1[SH:50].C(N(CC)CC)C>CN(C)C=O>[F:41][C:36]1[CH:35]=[C:34]([NH:33][C:32]([CH2:31][N+:28]2[CH:27]=[CH:26][C:25]([CH2:24][N:21]3[CH2:22][CH2:23]/[C:19](=[CH:18]\[C:10]4[CH2:9][S:8][C@H:7]5[N:12]([C:13](=[O:14])[C@H:6]5[NH:5][C:3](=[O:4])[CH2:2][S:50][C:46]5[N:45]([CH3:44])[CH:49]=[N:48][N:47]=5)[C:11]=4[C:15]([O-:17])=[O:16])/[C:20]3=[O:43])=[CH:30][CH:29]=2)=[O:42])[CH:39]=[CH:38][C:37]=1[OH:40]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 86757452HCID 86757452, VerbindungHCID 178481306HCID 178481306, Verbindung

Produkt 1

HCID 86757454HCID 86757454, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 230.0 mg (0.34 mmol) (E)-(6R,7R)-7-(2-Bromo-acetylamino)-3-(1-[1-[(3-fluoro-4-hydroxy-phenylcarbamoyl)-methyl]-pyridin-1-ium-4-ylmethyl]-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate in 5 ml N,N-dimethylformamide was added 40.0 mg (0.37 mmol) 4-methyl-4H-[1,2,4]triazole-3-thiol. After 1 h 47.0 μl (0.34 mmol) triethyl amine was added and stirring was continued for 12 h. The solution was poured on diethyl ether and the resulting solid was purified by column chromatography on MCI gel (75-150μ, Mitsubishi Kasei Corporation) with a gradient of water:acetonitrile (1:0, 4:1, 3:1, 2:1). The organic solvent was stripped off at a rotary evaporator and the aqueous phase was freeze-dried.

Aufarbeitung

  1. additionThe solution was poured on diethyl ether
  2. customthe resulting solid was purified by column chromatography on MCI gel (75-150μ, Mitsubishi Kasei Corporation) with a gradient of water:acetonitrile (1:0, 4:1, 3:1, 2:1)
  3. customThe organic solvent was stripped off at a rotary evaporator
  4. customthe aqueous phase was freeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-b847c183106a42afa46398c0c3aee53d
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06294668B1

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